Pesticidal compounds based on arylthiosulfonamide derivatives

ABSTRACT

The present invention provides compounds of formula (I) wherein R 1 , R 2 , R 3 , R 4 , n, A 1 , A 2 , A 3 , Y 1 , Y 2 , and Y 3  are as defined in the claims. The invention also relates to processes and intermediates for preparing these compounds, to insecticidal, acaricidal, nematicidal and molluscicidal compositions comprising these compounds and to methods of using these compounds to control insect, acarine, nematode and mollusc pests.

RELATED APPLICATION INFORMATION

This application is a 371 of International Application No.PCT/EP2013/074398, filed 21 Nov. 2013, which claims priority to EPPatent Application No. 121936157.7 filed 21 Nov. 2012; and Indian PatentApplication No. 3577/DEL/2012 filed 21 Nov. 2012, the contents of whichare incorporated herein by reference herein.

The present invention relates to certain arylthiosulfonamides andderivatives thereof, to processes and intermediates for preparing thesecompounds, to insecticidal, acaricidal, nematicidal and molluscicidalcompositions comprising these compounds and to methods of using thesecompounds to control insect, acarine, nematode and mollusc pests.

Certain compounds with insecticidal properties are disclosed, forexample, in JP2007106756. However there is a continuing need to find newbiologically active compounds as well as new biologically activecompounds displaying superior properties for use as agrochemical activeingredients, for example greater biological activity, different spectrumof activity, increased safety profile, or increased biodegradability.

It has now surprisingly been found that certain orthosubstitutedarylthiosulfonamides have highly potent insecticidal properties.

Accordingly in a first aspect the invention provides compounds offormula I

wherein

-   A¹ is C—R^(5b);-   A², A³ and A⁴ are independently of one another C—H, C—R^(5a) or    nitrogen;-   Y₁—Y₂—Y₃ is —C═N—O—, —C═N—S—, —C═N—CH₂—, —C═CH—O— or —N—CH₂—CH₂—,    —C═CH—S—;-   n is 0, 1 or 2;-   R¹ is hydrogen, C₁-C₈alkyl, C₁-C₈alkoxy, C₁-C₈alkylcarbonyl or    C₁-C₈alkoxycarbonyl;-   R² is hydrogen, C₁-C₈alkyl or C₁-C₈alkyl substituted by one to five    R⁶, C₂-C₈alkenyl or C₂-C₈alkenyl substituted by one to five R⁶,    C₂-C₈alkynyl or C₂-C₈alkynyl substituted by one to five R⁶,    C₃-C₁₀cycloalkyl or C₃-C₁₀cycloalkyl substituted by one to five R⁷,    aryl-C₁-C₄alkylene or aryl-C₁-C₄alkylene wherein the aryl moiety is    substituted by one to five R⁸, heterocyclyl-C₁-C₄alkylene or    heterocyclyl-C₁-C₁-C₄alkylene wherein the heterocyclyl moiety is    substituted by one to five R⁸, aryl or aryl substituted by one to    five R⁸, heterocyclyl or heterocyclyl substituted by one to five R⁸;    or R¹ and R² together with the nitrogen atom to which they are bound    form a 4- to 7-membered cycle containing carbon atoms as ring    members and optionally containing one oxygen atom or one sulfur atom    optionally oxidised as a ring member and wherein the cycle is    optionally substituted by 1 to 5 groups independently selected from    halogen, C₁-C₄alkyl and C₁-C₄alkoxy;-   R³ is C₁-C₈haloalkyl;-   R⁴ is aryl or aryl substituted by one to five R⁹, or heteroaryl or    heteroaryl substituted by one to five R⁹;-   each R^(5a) is independently halogen, cyano, nitro, C₁-C₈alkyl,    C₁-C₈haloalkyl, C₂-C₈alkenyl, C₂-C₈haloalkenyl, C₂-C₈alkynyl,    C₂-C₈haloalkynyl, C₃-C₁₀cycloalkyl, C₁-C₈alkoxy, C₁-C₈haloalkoxy,    C₁-C₈alkylthio, C₁-C₈haloalkylthio, C₁-C₈alkylsulfinyl-,    C₁-C₈haloalkylsulfinyl-, C₁-C₈alkylsulfonyl- or    C₁-C₈haloalkylsulfonyl-;-   R^(5b) is halogen, C₁-C₈alkyl, C₁-C₈haloalkyl, C₂-C₈alkenyl,    C₂-C₈haloalkenyl, C₂-C₈alkynyl, C₂-C₈haloalkynyl, C₃-C₁₀cycloalkyl    or C₃-C₁₀cycloalkyl substituted by one to five R⁷,-   or R^(5a) and R^(5b) on adjacent carbon atoms together form a    —CH═CH—CH═CH— bridge or a —N═CH—CH═CH— bridge;-   each R⁶ is independently halogen, cyano, nitro, hydroxy,    C₁-C₈alkoxy, C₁-C₈haloalkoxy, C₁-C₈alkylcarbonyl,    C₁-C₈alkoxycarbonyl, mercapto, C₁-C₈alkylthio, C₁-C₈haloalkylthio,    C₁-C₈alkylsulfinyl, C₁-C₈haloalkylsulfinyl, C₁-C₈alkylsulfonyl, or    C₁-C₈haloalkylsulfonyl;-   each R⁷ is independently halogen, cyano, C₁-C₈alkyl or    C₁-C₈haloalkyl;-   each R⁸ and R⁹ is independently halogen, cyano, nitro, C₁-C₈alkyl,    C₁-C₈haloalkyl, C₂-C₈alkenyl, C₂-C₈haloalkenyl, C₂-C₈alkynyl,    C₂-C₈haloalkynyl, hydroxy, C₁-C₈alkoxy, C₁-C₈haloalkoxy, mercapto,    C₁-C₈alkylthio, C₁-C₈haloalkylthio, C₁-C₈alkylsulfinyl,    C₁-C₈haloalkylsulfinyl, C₁-C₈alkylsulfonyl, C₁-C₈haloalkylsulfonyl,    C₁-C₈alkylcarbonyl, C₁-C₈alkoxycarbonyl, aryl or aryl substituted by    one to five R¹⁰ or heterocyclyl or heterocyclyl substituted by one    to five R¹⁰;-   each R¹⁰ is independently halogen, cyano, nitro, C₁-C₄alkyl,    C₁-C₄haloalkyl, C₁-C₄alkoxy or C₁-C₄haloalkoxy;-   or a salt or N-oxide thereof.

In a further aspect the present invention relates to compounds offormula I

wherein

-   A¹ is C—R^(5b);-   A², A³ and A⁴ are independently of one another C—H, C—R^(5a) or    nitrogen;-   Y₁—Y₂—Y₃ is —C═N—O—, —C═N—S—, —C═N—CH₂—, —C═CH—O— or —N—CH₂—CH₂—;-   n is 0, 1 or 2;-   R¹ is hydrogen, C₁-C₈alkyl, C₁-C₈alkoxy, C₁-C₈alkylcarbonyl or    C₁-C₈alkoxycarbonyl;-   R² is hydrogen, C₁-C₈alkyl or C₁-C₈alkyl substituted by one to five    R⁶, C₂-C₈alkenyl or C₂-C₈alkenyl substituted by one to five R⁶,    C₂-C₈alkynyl or C₂-C₈alkynyl substituted by one to five R⁶,    C₃-C₁₀cycloalkyl or C₃-C₁₀cycloalkyl substituted by one to five R⁷,    aryl-C₁-C₄alkylene or aryl-C₁-C₄alkylene wherein the aryl moiety is    substituted by one to five R⁸, heterocyclyl-C₁-C₄alkylene or    heterocyclyl-C₁-C₄alkylene wherein the heterocyclyl moiety is    substituted by one to five R⁸, aryl or aryl substituted by one to    five R⁸, heterocyclyl or heterocyclyl substituted by one to five R⁸;-   or R¹ and R² together with the nitrogen atom to which they are bound    form a 4- to 7-membered cycle containing carbon atoms as ring    members and optionally containing one oxygen atom or one sulfur atom    optionally oxidised as a ring member and wherein the cycle is    optionally substituted by 1 to 5 groups independently selected from    halogen, C₁-C₄alkyl and C₁-C₄alkoxy;-   R³ is C₁-C₈haloalkyl;-   R⁴ is aryl or aryl substituted by one to five R⁹, or heteroaryl or    heteroaryl substituted by one to five R⁹;-   each R^(5a) is independently halogen, cyano, nitro, C₁-C₈alkyl,    C₁-C₈haloalkyl, C₂-C₈alkenyl, C₂-C₈haloalkenyl, C₂-C₈alkynyl,    C₂-C₈haloalkynyl, C₃-C₁₀cycloalkyl, C₁-C₈alkoxy, C₁-C₈haloalkoxy,    C₁-C₈alkylthio, C₁-C₈haloalkylthio, C₁-C₈alkylsulfinyl-,    C₁-C₈haloalkylsulfinyl-, C₁-C₈alkylsulfonyl- or    C₁-C₈haloalkylsulfonyl-;-   R^(5b) is halogen, C₁-C₈alkyl, C₁-C₈haloalkyl, C₂-C₈alkenyl,    C₂-C₈haloalkenyl, C₂-C₈alkynyl, C₂-C₈haloalkynyl, C₃-C₁₀cycloalkyl    or C₃-C₁₀cycloalkyl substituted by one to five R⁷,-   or R^(5a) and R^(5b) on adjacent carbon atoms together form a    —CH═CH—CH═CH— bridge or a —N═CH—CH═CH— bridge;-   each R⁶ is independently halogen, cyano, nitro, hydroxy,    C₁-C₈alkoxy, C₁-C₈haloalkoxy, C₁-C₈alkylcarbonyl,    C₁-C₈alkoxycarbonyl, mercapto, C₁-C₈alkylthio, C₁-C₈haloalkylthio,    C₁-C₈alkylsulfinyl, C₁-C₈haloalkylsulfinyl, C₁-C₈alkylsulfonyl, or    C₁-C₈haloalkylsulfonyl;-   each R⁷ is independently halogen, cyano, C₁-C₈alkyl or    C₁-C₈haloalkyl;-   each R⁸ and R⁹ is independently halogen, cyano, nitro, C₁-C₈alkyl,    C₁-C₈haloalkyl, C₂-C₈alkenyl, C₂-C₈haloalkenyl, C₂-C₈alkynyl,    C₂-C₈haloalkynyl, hydroxy, C₁-C₈alkoxy, C₁-C₈haloalkoxy, mercapto,    C₁-C₈alkylthio, C₁-C₈haloalkylthio, C₁-C₈alkylsulfinyl,    C₁-C₈haloalkylsulfinyl, C₁-C₈alkylsulfonyl, C₁-C₈haloalkylsulfonyl,    C₁-C₈alkylcarbonyl, C₁-C₈alkoxycarbonyl, aryl or aryl substituted by    one to five R¹⁰ or heterocyclyl or heterocyclyl substituted by one    to five R¹⁰;-   each R¹⁰ is independently halogen, cyano, nitro, C₁-C₄alkyl,    C₁-C₄haloalkyl, C₁-C₄alkoxy or C₁-C₄haloalkoxy;-   or a salt or N-oxide thereof.

The compounds of formula (I) may exist in different geometric or opticalisomers or tautomeric forms. This invention covers all such isomers andtautomers and mixtures thereof in all proportions as well as isotopicforms such as deuterated compounds.

The compounds of the invention may contain one or more asymmetric carbonatoms, for example, in the —CR³R⁴— group and may exist as enantiomers(or as pairs of diastereoisomers) or as mixtures of such. Further, whereany group is SO, the compounds of the invention are sulfoxides, whichcan also exist in two enantiomeric forms.

Alkyl groups (either alone or as part of a larger group, such as alkoxy,alkylthio, alkylsulfinyl, alkylsulfonyl, alkylcarbonyl oralkoxycarbonyl) can be in the form of a straight or branched chain andare, for example, methyl, ethyl, propyl, prop-2-yl, butyl, but-2-yl,2-methyl-prop-1-yl or 2-methyl-prop-2-yl. The alkyl groups arepreferably C₁-C₆, more preferably C₁-C₄, most preferably C₁-C₃ alkylgroups. Where an alkyl moiety is said to be substituted, the alkylmoiety is preferably substituted by one to four substituents, mostpreferably by one to three substituents.

Alkylene groups can be in the form of a straight or branched chain andare, for example, —CH₂—, —CH₂—CH₂—, —CH(CH₃)—, —CH₂—CH₂—CH₂—,—CH(CH₃)—CH₂— or —CH(CH₂CH₃)—. The alkylene groups are preferably C₁-C₃,more preferably C₁-C₂, most preferably C₁ alkylene groups.

Alkenyl groups can be in the form of straight or branched chains, andcan be, where appropriate, of either the (E)- or (Z)-configuration.Examples are vinyl and allyl. The alkenyl groups are preferably C₂-C₆,more preferably C₂-C₄, most preferably C₂-C₃ alkenyl groups. For theavoidance of doubt, alkenyl groups contain one or more carbon-carbondouble bonds, each of which may be located at any point on the chain.

Alkynyl groups can be in the form of straight or branched chains.Examples are ethynyl and propargyl. The alkynyl groups are preferablyC₂-C₆, more preferably C₂-C₄, most preferably C₂-C₃ alkynyl groups. Forthe avoidance of doubt, alkynyl groups contain one or more carbon-carbontriple bonds, each of which may be located at any point on the chain.

Halogen is fluorine, chlorine, bromine or iodine.

Haloalkyl groups (either alone or as part of a larger group, such ashaloalkoxy, haloalkylthio, haloalkylsulfinyl or haloalkylsulfonyl) arealkyl groups which are substituted by one or more of the same ordifferent halogen atoms and are, for example, difluoromethyl,trifluoromethyl, chlorodifluoromethyl or 2,2,2-trifluoro-ethyl.

Haloalkenyl groups are alkenyl groups which are substituted by one ormore of the same or different halogen atoms and are, for example,2,2-difluoro-vinyl or 1,2-dichloro-2-fluoro-vinyl.

Haloalkynyl groups are alkynyl groups which are substituted by one ormore of the same or different halogen atoms and are, for example,1-chloro-prop-2-ynyl.

Cycloalkyl groups or carbocyclic rings can be in mono- or bi-cyclic formand are, for example, cyclopropyl, cyclobutyl, cyclohexyl andbicyclo[2.2.1]heptan-2-yl. The cycloalkyl groups are preferably C₃-C₈,more preferably C₃-C₆ cycloalkyl groups. Where a cycloalkyl moiety issaid to be substituted, the cycloalkyl moiety is preferably substitutedby one to four substituents, most preferably by one to threesubstituents.

Aryl groups (either alone or as part of a larger group, such asaryl-alkylene) are aromatic ring systems which can be in mono-, bi- ortricyclic form. Examples of such rings include phenyl, naphthyl,anthracenyl, indenyl or phenanthrenyl. Preferred aryl groups are phenyland naphthyl, phenyl being most preferred. Where an aryl moiety is saidto be substituted, the aryl moiety is preferably substituted by one tofour substituents, most preferably by one to three substituents.

Heteroaryl groups (either alone or as part of a larger group, such asheteroaryl-alkylene) are aromatic ring systems containing at least oneheteroatom and consisting either of a single ring or of two or morefused rings. Preferably, single rings will contain up to threeheteroatoms and bicyclic systems up to four heteroatoms which willpreferably be chosen from nitrogen, oxygen and sulfur. Examples ofmonocyclic groups include pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl,pyrrolyl, pyrazolyl, imidazolyl, triazolyl (e.g. 1.2.4 triazoyl),furanyl, thiophenyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl,isothiazolyl and thiadiazolyl. Examples of bicyclic groups includepurinyl, quinolinyl, cinnolinyl, quinoxalinyl, indolyl, indazolyl,benzimidazolyl, benzothiophenyl and benzothiazolyl. Monocyclicheteroaryl groups are preferred, pyridyl being most preferred. Where aheteroaryl moiety is said to be substituted, the heteroaryl moiety ispreferably substituted by one to four substituents, most preferably byone to three substituents.

Heterocyclyl groups or heterocyclic rings (either alone or as part of alarger group, such as heterocyclyl-alkylene) are defined to includeheteroaryl groups and in addition their unsaturated or partiallyunsaturated analogues. Examples of monocyclic groups include isoxazolyl,thietanyl, pyrrolidinyl, tetrahydrofuranyl, [1,3]dioxolanyl,piperidinyl, piperazinyl, [1,4]dioxanyl, and morpholinyl or theiroxidised versions such as 1-oxo-thietanyl and 1,1-dioxo-thietanyl.Examples of bicyclic groups include 2,3-dihydro-benzofuranyl,benzo[1,4]dioxolanyl, benzo[1,3]dioxolanyl, chromenyl, and2,3-dihydro-benzo[1,4]dioxinyl. Where a heterocyclyl moiety is said tobe substituted, the heterocyclyl moiety is preferably substituted by oneto four substituents, most preferably by one to three substituents.

Preferred values of A¹, A², A³, A⁴, n, R¹, R², R³, R⁴, Y¹, Y², Y³,R^(5a), R^(5b), R⁶, R⁷, R⁸, R⁹, R¹⁰ and R¹² are, in any combination, asset out below.

Preferably no more than two of A², A³ and A⁴ are nitrogen.

Preferably A² is C—H, C—R^(5a) or N, more preferably A² is C—H orC—R^(5a) , most preferably A² is C—H.

Preferably A³ is C—H or N, most preferably A³ is C—H.

Preferably A⁴ is C—H or N, most preferably A⁴ is C—H.

In one group of compounds A², A³ and A⁴ are C—H or N, wherein no morethan two of A², A³ and A⁴ are N and wherein A³ and A⁴ are not both N.Preferably A² is C—H and A³ and A⁴ are C—H or one of A³ and A⁴ is N.More preferably A², A³ and A⁴ are C—H.

Preferably R¹ is hydrogen, methyl, ethyl, methylcarbonyl ormethoxycarbonyl, more preferably hydrogen, methyl or ethyl, even morepreferably hydrogen or methyl, most preferably hydrogen.

Preferably, R² is C₁-C₈alkyl or C₁-C₈alkyl substituted by one to fiveR⁶, C₂-C₈alkenyl or C₂-C₈alkenyl substituted by one to five R⁶,C₂-C₈alkynyl or C₂-C₈alkynyl substituted by one to five R⁶,C₃-C₁₀cycloalkyl or C₃-C₁₀cycloalkyl substituted by one to five R⁷,aryl-C₁-C₄alkylene or aryl-C₁-C₄alkylene wherein the aryl moiety issubstituted by one to five R⁸, heterocyclyl-C₁-C₄alkylene orheterocyclyl-C₁-C₄alkylene wherein the heterocyclyl moiety issubstituted by one to five R⁸, aryl or aryl substituted by one to fiveR⁸, heterocyclyl or heterocyclyl substituted by one to five R⁸, whereineach aryl group is a phenyl group and each heterocyclyl group isindependently selected from pyridyl, pyridazinyl, pyrimidinyl,pyrazinyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl,tetrahydrothiophenyl, tetrazolyl, furanyl, thiophenyl, oxazolyl,isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl,quinolinyl, cinnolinyl, quinoxalinyl, indolyl, indazolyl,benzimidazolyl, benzothiophenyl, benzothiazolyl, oxetanyl, thietanyl,oxo-thietanyl, dioxo-thietanyl, pyrrolidinyl, tetrahydrofuranyl,[1,3]dioxolanyl, piperidinyl, piperazinyl, [1,4]dioxanyl, morpholinyl,2,3-dihydro-benzofuranyl, benzo[1,3]dioxolanyl, and2,3-dihydro-benzo-[1,4]dioxinyl.

More preferably R² is C₁-C₈alkyl or C₁-C₈alkyl substituted by one tofive R⁶, C₂-C₈alkenyl or C₂-C₈alkenyl substituted by one to five R⁶,C₂-C₈alkynyl or C₂-C₈alkynyl substituted by one to five R⁶,C₃-C₁₀cycloalkyl or C₃-C₁₀cycloalkyl substituted by one to five R⁷,phenyl-C₁-C₄alkylene or phenyl-C₁-C₄alkylene wherein the phenyl moietyis substituted by one to five R⁸, phenyl or phenyl substituted by one tofive R⁸, pyridyl-C₁-C₄alkylene or pyridyl-C₁-C₄alkylene wherein thepyridyl moiety is substituted by one to four R⁸, pyridyl or pyridylsubstituted by one to four R⁸, oxetanyl-C₁-C₄alkylene oroxetanyl-C₁-C₄alkylene wherein the oxetanyl moiety is substituted by oneto five R⁸, oxetanyl or oxetanyl substituted by one to five R⁸,thietanyl-C₁-C₄alkylene or thietanyl-C₁-C₄alkylene wherein the thietanylmoiety is substituted by one to five R⁸, thietanyl or thietanylsubstituted by one to five R⁸, oxo-thietanyl-C₁-C₄alkylene oroxo-thietanyl-C₁-C₄alkylene wherein the oxo-thietanyl moiety issubstituted by one to five R⁸, oxo-thietanyl or oxo-thietanylsubstituted by one to five R⁸, dioxo-thietanyl-C₁-C₄alkylene ordioxo-thietanyl-C₁-C₄alkylene wherein the dioxo-thietanyl moiety issubstituted by one to five R⁸, dioxo-thietanyl or dioxo-thietanylsubstituted by one to five R⁸, furanyl-C₁-C₄alkylene orfuranyl-C₁-C₄alkylene wherein the furanyl moiety is substituted by oneto four R⁸, tetrahydrofuranyl or tetrahydrofuranyl substituted by one tofive R⁸.

More preferably R² is C₁-C₄alkyl or C₁-C₄alkyl substituted by one tofive groups independently selected from halogen, cyano, C₁-C₄alkoxy andC₁-C₄alkylthio, C₂-C₄alkenyl or C₂-C₄alkenyl substituted by one to fivehalogen, C₂-C₄alkynyl or C₂-C₄alkynyl substituted by one to fivehalogen, C₃-C₆cycloalkyl or C₃-C₆cycloalkyl substituted by one to fivegroups independently selected from halogen, methyl and halomethyl,phenyl-C₁-C₂alkylene or phenyl-C₁-C₂alkylene wherein the phenyl moietyis optionally substituted by one to three substituents independentlyselected from halogen, cyano, C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxyand C₁-C₄haloalkoxy, pyridyl-C₁-C₂alkylene or pyridyl-C₁-C₂alkylenewherein the pyridyl moiety is optionally substituted by one to threesubstituents independently selected from halogen, cyano, C₁-C₄alkyl,C₁-C₄haloalkyl, C₁-C₄alkoxy and C₁-C₄haloalkoxy, thietanyl,oxo-thietanyl, dioxo-thietanyl, oxetanyl, tetrahydrofuranyl,thietanyl-methyl, oxo-thietanyl-methyl, dioxo-thietanyl-methyl,oxetanyl-methyl.

Even more preferably R² is is C₁-C₄alkyl or C₁-C₄alkyl substituted byone to five groups independently selected from halogen, cyano, methoxyand methylthio, C₂-C₄alkenyl or C₂-C₄alkenyl substituted by one to fivehalogen, C₂-C₄alkynyl or C₂-C₄alkynyl substituted by one to fivehalogen, C₃-C₄cycloalkyl or C₃-C₄cycloalkyl substituted by one to fivegroups independently selected from halogen, methyl and halomethyl,pyridylmethyl or pyridylmethyl wherein the pyridyl moiety is substitutedwith one to four groups selected from halogen, cyano, methyl,halomethyl, methoxy and halomethoxy.

Most preferably R² is methyl, ethyl, propyl, butyl, fluoroethyl,fluoropropyl, fluorobutyl, difluoroethyl, difluoropropyl, difluorobutyl,trifluoroethyl, trifluoropropyl, trifluorobutyl, cyclopropyl,cyclobutyl, allyl, propargyl or pyridylmethyl.

In one embodiment R¹ and R² together with the nitrogen atom to whichthey are bound form a 4- to 7-membered cycle containing carbon atoms asring members and optionally containing one oxygen atom or one sulfuratom optionally oxidized (e.g. —S(O)— or —S(O₂)—) as a ring member andwherein the cycle is optionally substituted by 1 to 5 groupsindependently selected from halogen C₁-C₄alkyl and C₁-C₄alkoxy.Preferably R¹ and R² together with the nitrogen atom to which they arebound form a 4- to 7-membered cycle containing carbon atoms as ringmembers and optionally containing one oxygen atom as a ring member.Preferably R¹ and R² together with the nitrogen atom to which they arebound form a ring fragment selected from —(CH₂)₃—, —(CH₂)₄—, —(CH₂)₅—,and —(CH₂)₂O(CH₂)₂—.

Preferably R³ is chlorodifluoromethyl or trifluoromethyl, mostpreferably trifluoromethyl.

Preferably R⁴ is aryl or aryl substituted by one to three R⁹, morepreferably R⁴ is phenyl or phenyl substituted by one to three R⁹, evenmore preferably R⁴ is phenyl substituted by one to three R⁹, morepreferably R⁴ is 3,5-dichlorophenyl-, 3-chloro-4-fluorophenyl-,3-fluoro-4-chlorophenyl-, 3,4-dichlorophenyl-, 3-chloro-4-bromophenyl-,3,5-dichloro-4-fluorophenyl-, 3,4,5-trichlorophenyl-,3,5-dichloro-4-iodophenyl-, 3,4,5-trifluorophenyl-,3-chloro-5-bromophenyl-, 3-chloro-5-fluorophenyl-,3-chloro-5-(trifluoromethyl)phenyl-,3,4-dichloro-5-(trifluoromethyl)phenyl-,3,5-bis(trifluoromethyl)phenyl-,4-chloro-3,5-bis(trifluoromethyl)phenyl-, 3-(trifluoromethyl)phenyl-,2,6-dichloro-4-pyridyl-, 2,6-bis(trifluoromethyl)-4-pyridyl-,3,5-dichloro-4-bromophenyl-, 3-bromo-5-(trifluoromethyl)phenyl-,3,5-dibromophenyl, more preferably 3,5-dichlorophenyl-,3-chloro-5-bromophenyl-, 3-chloro-5-(trifluoromethyl)phenyl-,3,5-dichloro-4-fluorophenyl-, 3,4,5-trichlorophenyl-,3,5-bis(trifluoromethyl)phenyl-, 3-(trifluoromethyl)phenyl-,2,6-dichloro-4-pyridyl-, 2,6-bis(trifluoromethyl)-4-pyridyl-,3,5-dichloro-4-bromophenyl-, 3-bromo-5-(trifluoromethyl)phenyl-,3,5-dibromophenyl-, or 3,4-dichlorophenyl-.In one group of componds R⁴is group A1

wherein X is C—R¹² or nitrogen (preferably C—R¹²) and each R¹² isindependently hydrogen, halogen or trihalomethyl, wherein at least twoR¹² are not hydrogen.

Preferably each R^(5a) is independently halogen, cyano, nitro,C₁-C₈alkyl, C₃-C₈cycloalkyl, C₁-C₈haloalkyl, C₂-C₈alkenyl, morepreferably halogen, cyano, nitro, C₁-C₈alkyl, C₂-C₈alkenyl,C₃-C₈cycloalkyl, C₁-C₈haloalkyl, even more preferably bromo, chloro,fluoro, cyano, nitro, methyl, ethyl, trifluoromethyl, cyclopropyl,vinyl, most preferably bromo, chloro, fluoro, cyclopropyl,trifluoromethyl, vinyl, methyl or ethyl.

Preferably R^(5b) is halogen, C₁-C₈alkyl, C₃-C₈cycloalkyl,C₁-C₈haloalkyl, C₂-C₈alkenyl, more preferably bromo, chloro, fluoro,cyano, nitro, methyl, ethyl, trifluoromethyl, cyclopropyl, vinyl, evenmore preferably bromo, chloro, fluoro, cyclopropyl, trifluoromethyl,vinyl or methyl, most preferably halogen or methyl. In one group ofcompounds R^(5b) is bromo. In one group of compounds R^(5b) is chloro.In one group of compounds R^(5b) is methyl. In one group of compoundsR^(5b) is chloro, bromo or methyl. In one group of compounds R^(5b) ischloro or bromo.

Preferably each R⁶ is independently halogen, nitro, cyano, C₁-C₄alkyl,C₁-C₄haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylthio, morepreferably bromo, chloro, fluoro, cyano, nitro, methyl, ethyl,trifluoromethyl, methoxy, difluoromethoxy, trifluoromethoxy, methylthio,even more preferably chloro, fluoro, cyano, nitro, methyl, ethyl,trifluoromethyl, methoxy, trifluoromethoxy or methylthio, mostpreferably bromo, chloro, fluoro, or trifluoromethyl.

Preferably each R⁷ is independently chloro, fluoro, cyano, methyl orhalomethyl, most preferably fluoro or methyl.

Preferably each R⁸ is independently halogen, cyano, nitro, C₁-C₈alkyl,C₁-C₈haloalkyl, C₂-C₈alkenyl, C₂-C₈haloalkenyl, C₂-C₈alkynyl,C₂-C₈haloalkynyl, hydroxy, C₁-C₈alkoxy, C₁-C₈haloalkoxy, mercapto,C₁-C₈alkylthio, C₁-C₈haloalkylthio, C₁-C₈alkylsulfinyl,C₁-C₈haloalkylsulfinyl, C₁-C₈alkylsulfonyl, C₁-C₈haloalkylsulfonyl,C₁-C₈alkylcarbonyl, C₁-C₈alkoxycarbonyl, aryl or aryl substituted by oneto five R¹⁰ or heterocyclyl or heterocyclyl substituted by one to fiveR¹⁰, more preferably each R⁸ is independently halogen, cyano, nitro,C₁-C₈alkyl, C₁-C₈haloalkyl, C₁-C₈alkoxy, C₁-C₈haloalkoxy orC₁-C₈alkylthio, more preferably halogen, cyano, C₁-C₄alkyl, C₁-C₄alkoxy,C₁-C₄haloalkyl or C₁-C₄haloalkoxy, even more preferably halogen, cyano,methyl, methoxy, halomethyl or halomethoxy, even more preferablyhalogen, cyano, methoxy, methyl, or trifluoromethyl, most preferablyhalogen, cyano, methoxy, or trifluoromethyl.

Preferably each R⁹ is independently halogen, C₁-C₈alkyl, C₁-C₈haloalkyl,C₁-C₈alkoxy, C₁-C₈haloalkoxy, C₁-C₈alkylthio or C₁-C₈haloalkylthio, morepreferably bromo, chloro, fluoro, trifluoromethyl, methoxy ormethylthio, most preferably trifluoromethyl, bromo or chloro.

Preferably each R¹⁰ is independently bromo, chloro, fluoro, cyano,nitro, methyl, ethyl, trifluoromethyl, methoxy, difluoromethoxy ortrifluoromethoxy, more preferably bromo, chloro, fluoro, nitro ormethyl, most preferably chloro, fluoro or methyl.

In one group of compounds n is 0. In another group of compounds n is 1.In another group of compounds n is 2.

In one group of compounds R^(y)a and R^(5b) on adjacent carbon atomstogether form a —CH═CH—CH═CH— bridge or a —N═CH—CH═CH— bridge. Inanother group of compounds R^(5a) and R^(5b) on adjacent carbon atoms donot together form a —CH═CH—CH═CH— bridge or a —N═CH—CH═CH— bridge.

In one group of compounds the invention relates to compounds of formulaIAa wherein Y₁—Y₂—Y₃ is —C═N—O—, and wherein the definitions of theother substituents and preferred definitions thereof are as definedabove. A particularly preferred embodiment within this group ofcompounds is represented by compounds of formula IAb

wherein R³, R⁴, R^(5b), n, R¹ and R², including preferred definitionsthereof, are as defined for compounds of formula I. Preferably R^(5b) isbromo, chloro, fluoro, or methyl. In one group of compounds of formulaIAb R^(5b) is bromo or chloro.

In one group of compounds the invention relates to compounds of formulaIBa wherein Y₁—Y₂—Y₃ is —C═N—CH₂—, and wherein the definitions of theother substituents and preferred definitions thereof are as definedabove. A particularly preferred embodiment within this group ofcompounds is represented by compounds of formula IBb

wherein R³, R⁴, R^(5b), n, R¹ and R², including preferred definitionsthereof, are as defined for compounds of formula I. Preferably R^(5b) isbromo, chloro, fluoro, or methyl. In one group of compounds of formulaIBb R^(5b) is bromo or chloro.

In one group of compounds the invention relates to compounds of formulaICa wherein Y₁—Y₂—Y₃ is —C═CH—O—, and wherein the definitions of theother substituents and preferred definitions thereof are as definedabove. A particularly preferred embodiment within this group ofcompounds is represented by compounds of formula ICb

wherein R³, R⁴, R^(5b), n, R¹ and R², including preferred definitionsthereof, are as defined for compounds of formula I. Preferably R^(5b) isbromo, chloro, fluoro, or methyl. In one group of compounds of formulaICb R^(5b) is bromo or chloro.

In one group of compounds the invention relates to compounds of formulaIDa wherein Y₁—Y₂—Y₃ is —N—CH₂—CH₂—, and wherein the definitions of theother substituents and preferred definitions thereof are as definedabove. A particularly preferred embodiment within this group ofcompounds is represented by compounds of formula IDb

wherein R³, R⁴, R^(5b), n, R¹ and R², including preferred definitionsthereof, are as defined for compounds of formula I. Preferably R^(5b) isbromo, chloro, fluoro, or methyl. In one group of compounds of formulaIDb R^(5b) is bromo or chloro.

In one group of compounds the invention relates to compounds of formulaIEa wherein Y₁—Y₂—Y₃ is —C═N—S—, and wherein the definitions of theother substituents and preferred definitions thereof are as definedabove. A particularly preferred embodiment within this group ofcompounds is represented by compounds of formula IEb

wherein R³, R⁴, R^(5b), n, R¹ and R², including preferred definitionsthereof, are as defined for compounds of formula I. Preferably R^(5b) isbromo, chloro, fluoro, or methyl. In one group of compounds of formulaIEb R^(5b) is bromo or chloro.

In one group of compounds the invention relates to compounds of formulaIFb

wherein R¹, R², R³, R⁴, R^(5b) and n, including preferred definitionsthereof, are as defined for compounds of formula I. Preferably R^(5b) isbromo, chloro, fluoro, or methyl. In one group of compounds of formulaIa R^(5b) is bromo or chloro.

Compounds in which Y₁—Y₂—Y₃ is —C═N—O— are preferred.

In one group of compounds A² is C—H and A³ and A⁴ are C—H or one of A³and A⁴ is N; R³ is chlorodifluoromethyl or trifluoromethyl; R⁴ is3,5-dibromo -phenyl, 3,5-dichloro-phenyl, 3,5-bis-(trifluoromethyl)-phenyl,4-bromo-3,5-dichlorophenyl,3,5-dichloro-4-fluoro, 3-bromo-5-(trifluoromethyl)phenyl- or3,4,5-trichloro-phenyl.

In one group of compounds A² is C—H and A³ and A⁴ are C—H or one of A³and A⁴ is N; R¹ is H, R³ is chlorodifluoromethyl or trifluoromethyl; R⁴is 3,5-dibromo-phenyl, 3,5-dichloro-phenyl, 3,5-bis-(trifluoromethyl)-phenyl,4-bromo-3,5-dichlorophenyl,3,5-dichloro-4-fluoro, 3-bromo-5-(trifluoromethyl)phenyl- or3,4,5-trichloro-phenyl.

In one group of compounds A², A³ and A⁴ are C—H; R¹ is H, R³ ischlorodifluoromethyl or trifluoromethyl; R⁴ is 3,5-dibromo-phenyl,3,5-dichloro-phenyl, 3,5-bis-(trifluoromethyl)-phenyl,4-bromo-3,5-dichlorophenyl, 3,5-dichloro-4-fluoro,3-bromo-5-(trifluoromethyl)phenyl- or 3,4,5-trichloro -phenyl.

In one group of compounds A², A³ and A⁴ are C—H; R¹ is H, R³ ischlorodifluoromethyl or trifluoromethyl; R⁴ is 3,5-dibromo-phenyl,3,5-dichloro-phenyl, 3,5-bis-(trifluoromethyl)-phenyl,4-bromo-3,5-dichlorophenyl, 3,5-dichloro-4-fluoro,3-bromo-5-(trifluoromethyl)phenyl- or 3,4,5-trichloro -phenyl; R^(5b) isbromo, chloro, fluoro, or methyl.

In one group of compounds A¹ is C—R^(5b); A², A³ and A⁴ are C—H;Y₁—Y₂—Y₃ is —C═N—O—, —C═N—S—, —C═N—CH₂—, —C═CH—S— or —N—CH₂—CH₂—; R¹ ishydrogen; R² is C₁-C₄alkyl or C₁-C₄alkyl substituted by one to fivegroups independently selected from halogen, cyano, C₁-C₄alkoxy andC₁-C₄alkylthio, C₂-C₄alkenyl or C₂-C₄alkenyl substituted by one to fivehalogen, C₂-C₄alkynyl or C₂-C₄alkynyl substituted by one to fivehalogen, C₃-C₆cycloalkyl or C₃-C₆cycloalkyl substituted by one to fivegroups independently selected from halogen, methyl and halomethyl,phenyl-C₁-C₂alkylene or phenyl-C₁-C₂alkylene wherein the phenyl moietyis optionally substituted by one to three substituents independentlyselected from halogen, cyano, C₁-C₄alkoxy, C₁-C₄haloalkyl andC₁-C₄haloalkoxy, pyridyl-C₁-C₂alkylene or pyridyl-C₁-C₂alkylene whereinthe pyridyl moiety is optionally substituted by one to threesubstituents independently selected from halogen, cyano, C₁-C₄alkoxy,C₁-C₄haloalkyl and C₁-C₄haloalkoxy, thietanyl, oxo-thietanyl,dioxo-thietanyl, oxetanyl, tetrahydrofuranyl, thietanyl-methyl,oxo-thietanyl, dioxo-thietanyl-methyl, oxetanyl-methyl; or R¹ and R²together with the nitrogen atom to which they are bound form a 4- to7-membered cycle containing carbon atoms as ring members and optionallycontaining one oxygen atom as a ring member; R³ is chlorodifluoromethylor trifluoromethyl; R⁴ is group A1

wherein X is C—R¹² or nitrogen (preferably C—R¹²) and each R¹² isindependently hydrogen, halogen or trihalomethyl, wherein at least twoR¹² are not hydrogen; R^(5b) is chloro, bromo or methyl.

In one group of compounds A¹ is C—R^(5b); A², A³ and A⁴ are C—H;Y₁—Y₂—Y₃ is —C═N—O; R¹ is hydrogen; R² is C₁-C₄alkyl or C₁-C₄alkylsubstituted by one to five groups independently selected from halogen,cyano, C₁-C₄alkoxy and C₁-C₄alkylthio, C₂-C₄alkenyl or C₂-C₄alkenylsubstituted by one to five halogen, C₂-C₄alkynyl or C₂-C₄alkynylsubstituted by one to five halogen, C₃-C₆cycloalkyl or C₃-C₆cycloalkylsubstituted by one to five groups independently selected from halogen,methyl and halomethyl, phenyl-C₁-C₂alkylene or phenyl-C₁-C₂alkylenewherein the phenyl moiety is optionally substituted by one to threesubstituents independently selected from halogen, cyano, C₁-C₄alkoxy,C₁-C₄haloalkyl and C₁-C₄haloalkoxy, pyridyl-C₁-C₂alkylene orpyridyl-C₁-C₂alkylene wherein the pyridyl moiety is optionallysubstituted by one to three substituents independently selected fromhalogen, cyano, C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy andC₁-C₄haloalkoxy, thietanyl, oxo-thietanyl, dioxo-thietanyl, oxetanyl,tetrahydrofuranyl, thietanyl-methyl, oxo-thietanyl,dioxo-thietanyl-methyl, oxetanyl-methyl, or or R¹ and R² together withthe nitrogen atom to which they are bound form a 4- to 7-membered cyclecontaining carbon atoms as ring members and optionally containing oneoxygen atom as a ring member; R³ is trifluoromethyl; R⁴ is group Alwherein X is C—R¹² or nitrogen (preferably C—R¹²) and each R¹² isindependently hydrogen, halogen or trihalomethyl, wherein at least twoR¹² are not hydrogen; R^(5b) is halogen or methyl.

In one group of compounds A is C—R^(5b); A², A³ and A⁴ are C—H; Y₁—Y₂—Y₃is —C═N—O —, —C═N—S—, —C═N—CH₂—, —C═CH—S— or —N—CH₂—CH₂-; R¹ ishydrogen; R² is C₁-C₄alkyl or C₁-C₄alkyl substituted by one to fivegroups independently selected from halogen, cyano, methoxy andmethylthio, C₂-C₄alkenyl or C₂-C₄alkenyl substituted by one to fivehalogen, C₂-C₄alkynyl or C₂-C₄alkynyl substituted by one to fivehalogen, C₃-C₄cycloalkyl or C₃-C₄cycloalkyl substituted by one to fivegroups independently selected from halogen, methyl and halomethyl,pyridylmethyl or pyridylmethyl wherein the pyridyl moiety is substitutedwith one to four groups selected from halogen, cyano, methyl,halomethyl, methoxy and halomethoxy; or R¹ and R² together with thenitrogen atom to which they are bound form a 4- to 7-membered cyclecontaining carbon atoms as ring members and optionally containing oneoxygen atom as a ring member; R³ is trifluoromethyl; R⁴ is group Al,wherein X is C—R¹² and each R¹² is independently hydrogen, halogen ortrihalomethyl, wherein at least two R¹² are not hydrogen; R^(5b) ishalogen or methyl.

In one group of compounds A¹ is C—R^(5b); A², A³ and A⁴ are C—H;Y₁—Y₂—Y₃ is —C═N—O—; R¹ is hydrogen; R² is is C₁-C₄alkyl or C₁-C₄alkylsubstituted by one to five groups independently selected from halogen,cyano, methoxy and methylthio, C₂-C₄alkenyl or C₂-C₄alkenyl substitutedby one to five halogen, C₂-C₄alkynyl or C₂-C₄alkynyl substituted by oneto five halogen, C₃-C₄cycloalkyl or C₃-C₄cycloalkyl substituted by oneto five groups independently selected from halogen, methyl andhalomethyl, pyridylmethyl or pyridylmethyl wherein the pyridyl moiety issubstituted with one to four groups selected from halogen, cyano,methyl, halomethyl, methoxy and halomethoxy; or R¹ and R² together withthe nitrogen atom to which they are bound form a 4- to 7-membered cyclecontaining carbon atoms as ring members and optionally containing oneoxygen atom as a ring member; R³ is trifluoromethyl; R⁴ is group Al,wherein X is C—R¹² and each R¹² is independently hydrogen, halogen ortrihalomethyl, wherein at least two R¹² are not hydrogen; R^(5b) ishalogen or methyl.

In one group of compounds A¹ is C—R^(5b); A², A³ and A⁴ are C—H;Y₁—Y₂—Y₃ is —C═N—O—, —C═N—S—, —C═N—CH₂—, —C═CH—S— or —N—CH₂—CH₂—; R¹ ishydrogen; R² is C₁-C₄alkyl or C₁-C₄alkyl substituted by one to fivegroups independently selected from halogen, cyano, methoxy andmethylthio, C₂-C₄alkenyl or C₂-C₄alkenyl substituted by one to fivehalogen, C₂-C₄alkynyl or C₂-C₄alkynyl substituted by one to fivehalogen, C₃-C₄cycloalkyl or C₃-C₄cycloalkyl substituted by one to fivegroups independently selected from halogen, methyl and halomethyl,pyridylmethyl or pyridylmethyl wherein the pyridyl moiety is substitutedwith one to four groups selected from halogen, cyano, methyl,halomethyl, methoxy and halomethoxy; R³ is trifluoromethyl; R⁴ is groupAl, wherein X is C—R¹² and each R¹² is independently hydrogen, halogenor trihalomethyl, wherein at least two R¹² are not hydrogen; R^(5b) ishalogen or methyl.

In one group of compounds A₁ is —CR^(5b); A², A³ and A⁴ are C—H;Y₁—Y₂—Y₃ is —C═N—O—; R¹ is hydrogen; R² is is C₁-C₄alkyl or C₁-C₄alkylsubstituted by one to five groups independently selected from halogen,cyano, methoxy and methylthio, C₂-C₄alkenyl or C₂-C₄alkenyl substitutedby one to five halogen, C₂-C₄alkynyl or C₂-C₄alkynyl substituted by oneto five halogen, C₃-C₄cycloalkyl or C₃-C₄cycloalkyl substituted by oneto five groups independently selected from halogen, methyl andhalomethyl, pyridylmethyl or pyridylmethyl wherein the pyridyl moiety issubstituted with one to four groups selected from halogen, cyano,methyl, halomethyl, methoxy and halomethoxy; R³ is trifluoromethyl; R⁴is group Al, wherein X is C—R¹² and each R¹² is independently hydrogen,halogen or trihalomethyl, wherein at least two R¹² are not hydrogen;R^(5b) is halogen or methyl.

In one group of compounds A¹ is C—R^(5b); A², A³ and A⁴ are C—H;Y₁—Y₂—Y₃ is —C═N—O—, —C═N—S—, —C═N—CH₂—, —C═CH—S— or —N—CH₂—CH₂-; R¹ ishydrogen; R² is methyl, ethyl, propyl, butyl, fluoroethyl, fluoropropyl,fluorobutyl, difluoroethyl, difluoropropyl, difluorobutyl,trifluoroethyl, trifluoropropyl, trifluorobutyl, cyclopropyl,cyclobutyl, allyl, propargyl, pyridylmethyl; R³ is trifluoromethyl; R⁴is group A1, wherein X is C—R¹² and each R¹² is independently hydrogen,halogen or trihalomethyl, wherein at least two R¹² are not hydrogen;R^(5b) is chloro, bromo or methyl.

In one group of compounds A¹ is C—R^(5b); A², A³ and A⁴ are C—H;Y₁—Y₂—Y₃ is —C═N—O—; R¹ is hydrogen; R² is methyl, ethyl, propyl, butyl,fluoroethyl, fluoropropyl, fluorobutyl, difluoroethyl, difluoropropyl,difluorobutyl, trifluoroethyl, trifluoropropyl, trifluorobutyl,cyclopropyl, cyclobutyl, allyl, propargyl, pyridylmethyl; R³ istrifluoromethyl; R⁴ is group Al, wherein X is C—R¹² and each R¹² isindependently hydrogen, halogen or trihalomethyl, wherein at least twoR¹² are not hydrogen; R^(5b) is chloro, bromo or methyl.

In a preferred embodiment where or R¹ and R² together with the nitrogenatom to which they are bound form a saturated or partially unsaturated4- to 7-membered cycle containing carbon atoms as ring members andoptionally containing one oxygen atom or one sulfur atom optionallyoxidised as a ring member and wherein the cycle is optionallysubstituted by 1 to 5 groups independently selected from halogen,C₁-C₄alkyl and C₁-C₄alkoxy;

Certain intermediates are novel and are also included as further aspectsof the invention.

In a further aspect the invention provides compounds of formula Int-I

wherein Y₁—Y₂—Y₃ is —C═N—O—, —C═N—S—, —C═N—CH₂—, —C═CH—S—, —C═CH—O—, or—N—CH₂—CH₂— and A¹, A², A³, A⁴, R³, R⁴ and n are as defined for thecompound of formula I, and R is OH or halogen, or a salt of N-oxidethereof. Preferred definitions of A¹, A², A³, A⁴, R³, R⁴ and n are asdefined for compounds of formula I. In one group of compounds of formulaInt-I Y₁—Y₂—Y₃ is —C═N—O—. In another group of compounds of formulaInt-I Y₁—Y₂—Y₃ is —C═N—CH₂. In another group of compounds of formulaInt-I Y₁—Y₂—Y₃ is —C═CH—O—. In another group of compounds of formulaInt-I Y₁—Y₂—Y₃ is —N—CH₂—CH₂—. In another group of compounds of formulaInt-I Y₁—Y₂—Y₃ is —C═N—S—. In another group of compounds of formulaInt-I Y₁—Y₂—Y₃ is —C═CH—S—,

In a further aspect the invention provides compounds of formula Int-II

wherein A¹, A², A³, A⁴, R¹, R² and n are as defined for the compound offormula I, and X^(B) is a leaving group, e.g. halogen, such as bromo, orX^(B) is cyano, formyl or acetyl, or a salt of N-oxide thereof.Preferred definitions of A¹, A², A³, A⁴, R¹, R² and n are as defined forcompounds of formula I.

In a further aspect the invention provides compounds of formula Int-III

wherein A¹, A², A³, A⁴ , R¹, R², and n are as defined for the compoundof formula I, or a salt of N-oxide thereof. Preferred definitions of A¹,A², A³, A⁴ , R¹, R², and n are as defined for compounds of formula I.

In a further aspect the invention provides compounds of formula Int-IV

wherein A¹, A², A³, A⁴, R¹, R², R³, R⁴ and n are as defined for thecompound of formula I, or a salt of N-oxide thereof. Preferreddefinitions of A¹, A², A³, A⁴, R¹, R² and n are as defined for compoundsof formula I.

A leaving group as referred to herein may be for example a halogen,C₁-C₈alkoxy, C₁-C₈alkylsulfonyloxy, C₁-C₈haloalkylsulfonyloxy,C₁-C₈arylsulfonyloxy, optionally substituted C₁-C₈arylsulfonyloxy (arylis preferably phenyl), diazonium salts (e.g. —N₂ ⁺Cl⁻, —N₂ ⁺BF₄ ⁻, —N₂⁺Br⁻, —N₂ ⁻PF₆ ⁻), phosphonate esters (e.g. —OP(O)(OR)₂, wherein R ismethyl or ethyl), preferably bromo, iodo, chloro,trifluoromethylsulfoxy, p-toluenesulfoxy, diazonium chloride.

Tables 1 to 312 below illustrate compounds of the invention.

TABLE P R5b n R2 1 methyl- 0 methyl- 2 chloro- 0 methyl- 3 bromo- 0methyl- 4 trifluoromethyl- 0 methyl- 5 methyl- 1 methyl- 6 chloro- 1methyl- 7 bromo- 1 methyl- 8 trifluoromethyl- 1 methyl- 9 methyl- 2methyl- 10 chloro- 2 methyl- 11 bromo- 2 methyl- 12 trifluoromethyl- 2methyl- 13 methyl- 0 ethyl- 14 chloro- 0 ethyl- 15 bromo- 0 ethyl- 16trifluoromethyl- 0 ethyl- 17 methyl- 1 ethyl- 18 chloro- 1 ethyl- 19bromo- 1 ethyl- 20 trifluoromethyl- 1 ethyl- 21 methyl- 2 ethyl- 22chloro- 2 ethyl- 23 bromo- 2 ethyl- 24 trifluoromethyl- 2 ethyl- 25methyl- 0 2-propyl- 26 chloro- 0 2-propyl- 27 bromo- 0 2-propyl- 28trifluoromethyl- 0 2-propyl- 29 methyl- 1 2-propyl- 30 chloro- 12-propyl- 31 bromo- 1 2-propyl- 32 trifluoromethyl- 1 2-propyl- 33methyl- 2 2-propyl- 34 chloro- 2 2-propyl- 35 bromo- 2 2-propyl- 36trifluoromethyl- 2 2-propyl- 37 methyl- 0 n-propyl- 38 chloro- 0n-propyl- 39 bromo- 0 n-propyl- 40 trifluoromethyl- 0 n-propyl- 41methyl- 1 n-propyl- 42 chloro- 1 n-propyl- 43 bromo- 1 n-propyl- 44trifluoromethyl- 1 n-propyl- 45 methyl- 2 n-propyl- 46 chloro- 2n-propyl- 47 bromo- 2 n-propyl- 48 trifluoromethyl- 2 n-propyl- 49methyl- 0 n-butyl- 50 chloro- 0 n-butyl- 51 bromo- 0 n-butyl- 52trifluoromethyl- 0 n-butyl- 53 methyl- 1 n-butyl- 54 chloro- 1 n-butyl-55 bromo- 1 n-butyl- 56 trifluoromethyl- 1 n-butyl- 57 methyl- 2n-butyl- 58 chloro- 2 n-butyl- 59 bromo- 2 n-butyl- 60 trifluoromethyl-2 n-butyl- 61 methyl- 0 s-butyl- 62 chloro- 0 s-butyl- 63 bromo- 0s-butyl- 64 trifluoromethyl- 0 s-butyl- 65 methyl- 1 s-butyl- 66 chloro-1 s-butyl- 67 bromo- 1 s-butyl- 68 trifluoromethyl- 1 s-butyl- 69methyl- 2 s-butyl- 70 chloro- 2 s-butyl- 71 bromo- 2 s-butyl- 72trifluoromethyl- 2 s-butyl- 73 methyl- 0 t-butyl 74 chloro- 0 t-butyl 75bromo- 0 t-butyl 76 trifluoromethyl- 0 t-butyl 77 methyl- 1 t-butyl 78chloro- 1 t-butyl 79 bromo- 1 t-butyl 80 trifluoromethyl- 1 t-butyl 81methyl- 2 t-butyl 82 chloro- 2 t-butyl 83 bromo- 2 t-butyl 84trifluoromethyl- 2 t-butyl 85 methyl- 0 2,2,2-trifluoro-ethyl- 86chloro- 0 2,2,2-trifluoro-ethyl- 87 bromo- 0 2,2,2-trifluoro-ethyl- 88trifluoromethyl- 0 2,2,2-trifluoro-ethyl- 89 methyl- 12,2,2-trifluoro-ethyl- 90 chloro- 1 2,2,2-trifluoro-ethyl- 91 bromo- 12,2,2-trifluoro-ethyl- 92 trifluoromethyl- 1 2,2,2-trifluoro-ethyl- 93methyl- 2 2,2,2-trifluoro-ethyl- 94 chloro- 2 2,2,2-trifluoro-ethyl- 95bromo- 2 2,2,2-trifluoro-ethyl- 96 trifluoromethyl- 22,2,2-trifluoro-ethyl- 97 methyl- 0 2,2-difluoro-ethyl- 98 chloro- 02,2-difluoro-ethyl- 99 bromo- 0 2,2-difluoro-ethyl- 100 trifluoromethyl-0 2,2-difluoro-ethyl- 101 methyl- 1 2,2-difluoro-ethyl- 102 chloro- 12,2-difluoro-ethyl- 103 bromo- 1 2,2-difluoro-ethyl- 104trifluoromethyl- 1 2,2-difluoro-ethyl- 105 methyl- 2 2,2-difluoro-ethyl-106 chloro- 2 2,2-difluoro-ethyl- 107 bromo- 2 2,2-difluoro-ethyl- 108trifluoromethyl- 2 2,2-difluoro-ethyl- 109 methyl- 0 2-fluoro-ethyl- 110chloro- 0 2-fluoro-ethyl- 111 bromo- 0 2-fluoro-ethyl- 112trifluoromethyl- 0 2-fluoro-ethyl- 113 methyl- 1 2-fluoro-ethyl- 114chloro- 1 2-fluoro-ethyl- 115 bromo- 1 2-fluoro-ethyl- 116trifluoromethyl- 1 2-fluoro-ethyl- 117 methyl- 2 2-fluoro-ethyl- 118chloro- 2 2-fluoro-ethyl- 119 bromo- 2 2-fluoro-ethyl- 120trifluoromethyl- 2 2-fluoro-ethyl- 121 methyl- 0 2-fluoropropyl- 122chloro- 0 2-fluoropropyl- 123 bromo- 0 2-fluoropropyl- 124trifluoromethyl- 0 2-fluoropropyl- 125 methyl- 1 2-fluoropropyl- 126chloro- 1 2-fluoropropyl- 127 bromo- 1 2-fluoropropyl- 128trifluoromethyl- 1 2-fluoropropyl- 129 methyl- 2 2-fluoropropyl- 130chloro- 2 2-fluoropropyl- 131 bromo- 2 2-fluoropropyl- 132trifluoromethyl- 2 2-fluoropropyl- 133 methyl- 0 3,3,3-trifluoro-propyl-134 chloro- 0 3,3,3-trifluoro-propyl- 135 bromo- 03,3,3-trifluoro-propyl- 136 trifluoromethyl- 0 3,3,3-trifluoro-propyl-137 methyl- 1 3,3,3-trifluoro-propyl- 138 chloro- 13,3,3-trifluoro-propyl- 139 bromo- 1 3,3,3-trifluoro-propyl- 140trifluoromethyl- 1 3,3,3-trifluoro-propyl- 141 methyl- 23,3,3-trifluoro-propyl- 142 chloro- 2 3,3,3-trifluoro-propyl- 143 bromo-2 3,3,3-trifluoro-propyl- 144 trifluoromethyl- 2 3,3,3-trifluoro-propyl-145 methyl- 0 3,3,3-trifluoro-butyl- 146 chloro- 03,3,3-trifluoro-butyl- 147 bromo- 0 3,3,3-trifluoro-butyl- 148trifluoromethyl- 0 3,3,3-trifluoro-butyl- 149 methyl- 13,3,3-trifluoro-butyl- 150 chloro- 1 3,3,3-trifluoro-butyl- 151 bromo- 13,3,3-trifluoro-butyl- 152 trifluoromethyl- 1 3,3,3-trifluoro-butyl- 153methyl- 2 3,3,3-trifluoro-butyl- 154 chloro- 2 3,3,3-trifluoro-butyl-155 bromo- 2 3,3,3-trifluoro-butyl- 156 trifluoromethyl- 23,3,3-trifluoro-butyl- 157 methyl- 0 2-cyanoethyl- 158 chloro- 02-cyanoethyl- 159 bromo- 0 2-cyanoethyl- 160 trifluoromethyl- 02-cyanoethyl- 161 methyl- 1 2-cyanoethyl- 162 chloro- 1 2-cyanoethyl-163 bromo- 1 2-cyanoethyl- 164 trifluoromethyl- 1 2-cyanoethyl- 165methyl- 2 2-cyanoethyl- 166 chloro- 2 2-cyanoethyl- 167 bromo- 22-cyanoethyl- 168 trifluoromethyl- 2 2-cyanoethyl- 169 methyl- 0cyanomethyl- 170 chloro- 0 cyanomethyl- 171 bromo- 0 cyanomethyl- 172trifluoromethyl- 0 cyanomethyl- 173 methyl- 1 cyanomethyl- 174 chloro- 1cyanomethyl- 175 bromo- 1 cyanomethyl- 176 trifluoromethyl- 1cyanomethyl- 177 methyl- 2 cyanomethyl- 178 chloro- 2 cyanomethyl- 179bromo- 2 cyanomethyl- 180 trifluoromethyl- 2 cyanomethyl- 181 methyl- 02-cyano-propan-2yl- 182 chloro- 0 2-cyano-propan-2yl- 183 bromo- 02-cyano-propan-2yl- 184 trifluoromethyl- 0 2-cyano-propan-2yl- 185methyl- 1 2-cyano-propan-2yl- 186 chloro- 1 2-cyano-propan-2yl- 187bromo- 1 2-cyano-propan-2yl- 188 trifluoromethyl- 1 2-cyano-propan-2yl-189 methyl- 2 2-cyano-propan-2yl- 190 chloro- 2 2-cyano-propan-2yl- 191bromo- 2 2-cyano-propan-2yl- 192 trifluoromethyl- 2 2-cyano-propan-2yl-193 methyl- 0 1-methoxy-prop-2-yl- 194 chloro- 0 1-methoxy-prop-2-yl-195 bromo- 0 1-methoxy-prop-2-yl- 196 trifluoromethyl- 01-methoxy-prop-2-yl- 197 methyl- 1 1-methoxy-prop-2-yl- 198 chloro- 11-methoxy-prop-2-yl- 199 bromo- 1 1-methoxy-prop-2-yl- 200trifluoromethyl- 1 1-methoxy-prop-2-yl- 201 methyl- 21-methoxy-prop-2-yl- 202 chloro- 2 1-methoxy-prop-2-yl- 203 bromo- 21-methoxy-prop-2-yl- 204 trifluoromethyl- 2 1-methoxy-prop-2-yl- 205methyl- 0 2-methylsulfanyl-ethyl- 206 chloro- 0 2-methylsulfanyl-ethyl-207 bromo- 0 2-methylsulfanyl-ethyl- 208 trifluoromethyl- 02-methylsulfanyl-ethyl- 209 methyl- 1 2-methylsulfanyl-ethyl- 210chloro- 1 2-methylsulfanyl-ethyl- 211 bromo- 1 2-methylsulfanyl-ethyl-212 trifluoromethyl- 1 2-methylsulfanyl-ethyl- 213 methyl- 22-methylsulfanyl-ethyl- 214 chloro- 2 2-methylsulfanyl-ethyl- 215 bromo-2 2-methylsulfanyl-ethyl- 216 trifluoromethyl- 2 2-methylsulfanyl-ethyl-217 methyl- 0 2-methylsulfanyl-prop-3-yl- 218 chloro- 02-methylsulfanyl-prop-3-yl- 219 bromo- 0 2-methylsulfanyl-prop-3-yl- 220trifluoromethyl- 0 2-methylsulfanyl-prop-3-yl- 221 methyl- 12-methylsulfanyl-prop-3-yl- 222 chloro- 1 2-methylsulfanyl-prop-3-yl-223 bromo- 1 2-methylsulfanyl-prop-3-yl- 224 trifluoromethyl- 12-methylsulfanyl-prop-3-yl- 225 methyl- 2 2-methylsulfanyl-prop-3-yl-226 chloro- 2 2-methylsulfanyl-prop-3-yl- 227 bromo- 22-methylsulfanyl-prop-3-yl- 228 trifluoromethyl- 22-methylsulfanyl-prop-3-yl- 229 methyl- 0 allyl- 230 chloro- 0 allyl-231 bromo- 0 allyl- 232 trifluoromethyl- 0 allyl- 233 methyl- 1 allyl-234 chloro- 1 allyl- 235 bromo- 1 allyl- 236 trifluoromethyl- 1 allyl-237 methyl- 2 allyl- 238 chloro- 2 allyl- 239 bromo- 2 allyl- 240trifluoromethyl- 2 allyl- 241 methyl- 0 3,3-dichloroallyl- 242 chloro- 03,3-dichloroallyl- 243 bromo- 0 3,3-dichloroallyl- 244 trifluoromethyl-0 3,3-dichloroallyl- 245 methyl- 1 3,3-dichloroallyl- 246 chloro- 13,3-dichloroallyl- 247 bromo- 1 3,3-dichloroallyl- 248 trifluoromethyl-1 3,3-dichloroallyl- 249 methyl- 2 3,3-dichloroallyl- 250 chloro- 23,3-dichloroallyl- 251 bromo- 2 3,3-dichloroallyl- 252 trifluoromethyl-2 3,3-dichloroallyl- 253 methyl- 0 2-butenyl- 254 chloro- 0 2-butenyl-255 bromo- 0 2-butenyl- 256 trifluoromethyl- 0 2-butenyl- 257 methyl- 12-butenyl- 258 chloro- 1 2-butenyl- 259 bromo- 1 2-butenyl- 260trifluoromethyl- 1 2-butenyl- 261 methyl- 2 2-butenyl- 262 chloro- 22-butenyl- 263 bromo- 2 2-butenyl- 264 trifluoromethyl- 2 2-butenyl- 265methyl- 0 2-chloroallyl- 266 chloro- 0 2-chloroallyl- 267 bromo- 02-chloroallyl- 268 trifluoromethyl- 0 2-chloroallyl- 269 methyl- 12-chloroallyl- 270 chloro- 1 2-chloroallyl- 271 bromo- 1 2-chloroallyl-272 trifluoromethyl- 1 2-chloroallyl- 273 methyl- 2 2-chloroallyl- 274chloro- 2 2-chloroallyl- 275 bromo- 2 2-chloroallyl- 276trifluoromethyl- 2 2-chloroallyl- 277 methyl- 0 propargyl- 278 chloro- 0propargyl- 279 bromo- 0 propargyl- 280 trifluoromethyl- 0 propargyl- 281methyl- 1 propargyl- 282 chloro- 1 propargyl- 283 bromo- 1 propargyl-284 trifluoromethyl- 1 propargyl- 285 methyl- 2 propargyl- 286 chloro- 2propargyl- 287 bromo- 2 propargyl- 288 trifluoromethyl- 2 propargyl- 289methyl- 0 but-2-ynyl- 290 chloro- 0 but-2-ynyl- 291 bromo- 0 but-2-ynyl-292 trifluoromethyl- 0 but-2-ynyl- 293 methyl- 1 but-2-ynyl- 294 chloro-1 but-2-ynyl- 295 bromo- 1 but-2-ynyl- 296 trifluoromethyl- 1but-2-ynyl- 297 methyl- 2 but-2-ynyl- 298 chloro- 2 but-2-ynyl- 299bromo- 2 but-2-ynyl- 300 trifluoromethyl- 2 but-2-ynyl- 301 methyl- 0but-3-ynyl- 302 chloro- 0 but-3-ynyl- 303 bromo- 0 but-3-ynyl- 304trifluoromethyl- 0 but-3-ynyl- 305 methyl- 1 but-3-ynyl- 306 chloro- 1but-3-ynyl- 307 bromo- 1 but-3-ynyl- 308 trifluoromethyl- 1 but-3-ynyl-309 methyl- 2 but-3-ynyl- 310 chloro- 2 but-3-ynyl- 311 bromo- 2but-3-ynyl- 312 trifluoromethyl- 2 but-3-ynyl- 313 methyl- 0 benzyl- 314chloro- 0 benzyl- 315 bromo- 0 benzyl- 316 trifluoromethyl- 0 benzyl-317 methyl- 1 benzyl- 318 chloro- 1 benzyl- 319 bromo- 1 benzyl- 320trifluoromethyl- 1 benzyl- 321 methyl- 2 benzyl- 322 chloro- 2 benzyl-323 bromo- 2 benzyl- 324 trifluoromethyl- 2 benzyl- 325 methyl- 0cyclopropyl- 326 chloro- 0 cyclopropyl- 327 bromo- 0 cyclopropyl- 328trifluoromethyl- 0 cyclopropyl- 329 methyl- 1 cyclopropyl- 330 chloro- 1cyclopropyl- 331 bromo- 1 cyclopropyl- 332 trifluoromethyl- 1cyclopropyl- 333 methyl- 2 cyclopropyl- 334 chloro- 2 cyclopropyl- 335bromo- 2 cyclopropyl- 336 trifluoromethyl- 2 cyclopropyl- 337 methyl- 0cyclobutyl- 338 chloro- 0 cyclobutyl- 339 bromo- 0 cyclobutyl- 340trifluoromethyl- 0 cyclobutyl- 341 methyl- 1 cyclobutyl- 342 chloro- 1cyclobutyl- 343 bromo- 1 cyclobutyl- 344 trifluoromethyl- 1 cyclobutyl-345 methyl- 2 cyclobutyl- 346 chloro- 2 cyclobutyl- 347 bromo- 2cyclobutyl- 348 trifluoromethyl- 2 cyclobutyl- 349 methyl- 0cyclopentyl- 350 chloro- 0 cyclopentyl- 351 bromo- 0 cyclopentyl- 352trifluoromethyl- 0 cyclopentyl- 353 methyl- 1 cyclopentyl- 354 chloro- 1cyclopentyl- 355 bromo- 1 cyclopentyl- 356 trifluoromethyl- 1cyclopentyl- 357 methyl- 2 cyclopentyl- 358 chloro- 2 cyclopentyl- 359bromo- 2 cyclopentyl- 360 trifluoromethyl- 2 cyclopentyl- 361 methyl- 0cyclopropyl-methyl- 362 chloro- 0 cyclopropyl-methyl- 363 bromo- 0cyclopropyl-methyl- 364 trifluoromethyl- 0 cyclopropyl-methyl- 365methyl- 1 cyclopropyl-methyl- 366 chloro- 1 cyclopropyl-methyl- 367bromo- 1 cyclopropyl-methyl- 368 trifluoromethyl- 1 cyclopropyl-methyl-369 methyl- 2 cyclopropyl-methyl- 370 chloro- 2 cyclopropyl-methyl- 371bromo- 2 cyclopropyl-methyl- 372 trifluoromethyl- 2 cyclopropyl-methyl-373 methyl- 0 cyclobutyl-methyl- 374 chloro- 0 cyclobutyl-methyl- 375bromo- 0 cyclobutyl-methyl- 376 trifluoromethyl- 0 cyclobutyl-methyl-377 methyl- 1 cyclobutyl-methyl- 378 chloro- 1 cyclobutyl-methyl- 379bromo- 1 cyclobutyl-methyl- 380 trifluoromethyl- 1 cyclobutyl-methyl-381 methyl- 2 cyclobutyl-methyl- 382 chloro- 2 cyclobutyl-methyl- 383bromo- 2 cyclobutyl-methyl- 384 trifluoromethyl- 2 cyclobutyl-methyl-385 methyl- 0 thietan-3-yl- 386 chloro- 0 thietan-3-yl- 387 bromo- 0thietan-3-yl- 388 trifluoromethyl- 0 thietan-3-yl- 389 methyl- 1thietan-3-yl- 390 chloro- 1 thietan-3-yl- 391 bromo- 1 thietan-3-yl- 392trifluoromethyl- 1 thietan-3-yl- 393 methyl- 2 thietan-3-yl- 394 chloro-2 thietan-3-yl- 395 bromo- 2 thietan-3-yl- 396 trifluoromethyl- 2thietan-3-yl- 397 methyl- 0 1-oxo-thietan-3-yl- 398 chloro- 01-oxo-thietan-3-yl- 399 bromo- 0 1-oxo-thietan-3-yl- 400trifluoromethyl- 0 1-oxo-thietan-3-yl- 401 methyl- 1 1-oxo-thietan-3-yl-402 chloro- 1 1-oxo-thietan-3-yl- 403 bromo- 1 1-oxo-thietan-3-yl- 404trifluoromethyl- 1 1-oxo-thietan-3-yl- 405 methyl- 2 1-oxo-thietan-3-yl-406 chloro- 2 1-oxo-thietan-3-yl- 407 bromo- 2 1-oxo-thietan-3-yl- 408trifluoromethyl- 2 1-oxo-thietan-3-yl- 409 methyl- 01,1-dioxo-thietan-3-yl- 410 chloro- 0 1,1-dioxo-thietan-3-yl- 411 bromo-0 1,1-dioxo-thietan-3-yl- 412 trifluoromethyl- 0 1,1-dioxo-thietan-3-yl-413 methyl- 1 1,1-dioxo-thietan-3-yl- 414 chloro- 11,1-dioxo-thietan-3-yl- 415 bromo- 1 1,1-dioxo-thietan-3-yl- 416trifluoromethyl- 1 1,1-dioxo-thietan-3-yl- 417 methyl- 21,1-dioxo-thietan-3-yl- 418 chloro- 2 1,1-dioxo-thietan-3-yl- 419 bromo-2 1,1-dioxo-thietan-3-yl- 420 trifluoromethyl- 2 1,1-dioxo-thietan-3-yl-421 methyl- 0 3-methyl-thietan-3-yl- 422 chloro- 03-methyl-thietan-3-yl- 423 bromo- 0 3-methyl-thietan-3-yl- 424trifluoromethyl- 0 3-methyl-thietan-3-yl- 425 methyl- 13-methyl-thietan-3-yl- 426 chloro- 1 3-methyl-thietan-3-yl- 427 bromo- 13-methyl-thietan-3-yl- 428 trifluoromethyl- 1 3-methyl-thietan-3-yl- 429methyl- 2 3-methyl-thietan-3-yl- 430 chloro- 2 3-methyl-thietan-3-yl-431 bromo- 2 3-methyl-thietan-3-yl- 432 trifluoromethyl- 23-methyl-thietan-3-yl- 433 methyl- 0 thietan-3-ylmethyl- 434 chloro- 0thietan-3-ylmethyl- 435 bromo- 0 thietan-3-ylmethyl- 436trifluoromethyl- 0 thietan-3-ylmethyl- 437 methyl- 1 thietan-3-ylmethyl-438 chloro- 1 thietan-3-ylmethyl- 439 bromo- 1 thietan-3-ylmethyl- 440trifluoromethyl- 1 thietan-3-ylmethyl- 441 methyl- 2 thietan-3-ylmethyl-442 chloro- 2 thietan-3-ylmethyl- 443 bromo- 2 thietan-3-ylmethyl- 444trifluoromethyl- 2 thietan-3-ylmethyl- 445 methyl- 0(1,1-dioxothietan-3-yl)methyl- 446 chloro- 0(1,1-dioxothietan-3-yl)methyl- 447 bromo- 0(1,1-dioxothietan-3-yl)methyl- 448 trifluoromethyl- 0(1,1-dioxothietan-3-yl)methyl- 449 methyl- 1(1,1-dioxothietan-3-yl)methyl- 450 chloro- 1(1,1-dioxothietan-3-yl)methyl- 451 bromo- 1(1,1-dioxothietan-3-yl)methyl- 452 trifluoromethyl- 1(1,1-dioxothietan-3-yl)methyl- 453 methyl- 2(1,1-dioxothietan-3-yl)methyl- 454 chloro- 2(1,1-dioxothietan-3-yl)methyl- 455 bromo- 2(1,1-dioxothietan-3-yl)methyl- 456 trifluoromethyl- 2(1,1-dioxothietan-3-yl)methyl- 457 methyl- 0 (1-oxothietan-3-yl)methyl-458 chloro- 0 (1-oxothietan-3-yl)methyl- 459 bromo- 0(1-oxothietan-3-yl)methyl- 460 trifluoromethyl- 0(1-oxothietan-3-yl)methyl- 461 methyl- 1 (1-oxothietan-3-yl)methyl- 462chloro- 1 (1-oxothietan-3-yl)methyl- 463 bromo- 1(1-oxothietan-3-yl)methyl- 464 trifluoromethyl- 1(1-oxothietan-3-yl)methyl- 465 methyl- 2 (1-oxothietan-3-yl)methyl- 466chloro- 2 (1-oxothietan-3-yl)methyl- 467 bromo- 2(1-oxothietan-3-yl)methyl- 468 trifluoromethyl- 2(1-oxothietan-3-yl)methyl- 469 methyl- 0 cis-1-oxo-thietan-3-yl- 470chloro- 0 cis-1-oxo-thietan-3-yl- 471 bromo- 0 cis-1-oxo-thietan-3-yl-472 trifluoromethyl- 0 cis-1-oxo-thietan-3-yl- 473 methyl- 1cis-1-oxo-thietan-3-yl- 474 chloro- 1 cis-1-oxo-thietan-3-yl- 475 bromo-1 cis-1-oxo-thietan-3-yl- 476 trifluoromethyl- 1 cis-1-oxo-thietan-3-yl-477 methyl- 2 cis-1-oxo-thietan-3-yl- 478 chloro- 2cis-1-oxo-thietan-3-yl- 479 bromo- 2 cis-1-oxo-thietan-3-yl- 480trifluoromethyl- 2 cis-1-oxo-thietan-3-yl- 481 methyl- 0cis-1-oxo-thietan-3-ylmethyl- 482 chloro- 0cis-1-oxo-thietan-3-ylmethyl- 483 bromo- 0 cis-1-oxo-thietan-3-ylmethyl-484 trifluoromethyl- 0 cis-1-oxo-thietan-3-ylmethyl- 485 methyl- 1cis-1-oxo-thietan-3-ylmethyl- 486 chloro- 1cis-1-oxo-thietan-3-ylmethyl- 487 bromo- 1 cis-1-oxo-thietan-3-ylmethyl-488 trifluoromethyl- 1 cis-1-oxo-thietan-3-ylmethyl- 489 methyl- 2cis-1-oxo-thietan-3-ylmethyl- 490 chloro- 2cis-1-oxo-thietan-3-ylmethyl- 491 bromo- 2 cis-1-oxo-thietan-3-ylmethyl-492 trifluoromethyl- 2 cis-1-oxo-thietan-3-ylmethyl- 493 methyl- 0(pyrid-2-yl)-methyl- 494 chloro- 0 (pyrid-2-yl)-methyl- 495 bromo- 0(pyrid-2-yl)-methyl- 496 trifluoromethyl- 0 (pyrid-2-yl)-methyl- 497methyl- 1 (pyrid-2-yl)-methyl- 498 chloro- 1 (pyrid-2-yl)-methyl- 499bromo- 1 (pyrid-2-yl)-methyl- 500 trifluoromethyl- 1(pyrid-2-yl)-methyl- 501 methyl- 2 (pyrid-2-yl)-methyl- 502 chloro- 2(pyrid-2-yl)-methyl- 503 bromo- 2 (pyrid-2-yl)-methyl- 504trifluoromethyl- 2 (pyrid-2-yl)-methyl- 505 methyl- 0(pyrid-3-yl)-methyl- 506 chloro- 0 (pyrid-3-yl)-methyl- 507 bromo- 0(pyrid-3-yl)-methyl- 508 trifluoromethyl- 0 (pyrid-3-yl)-methyl- 509methyl- 1 (pyrid-3-yl)-methyl- 510 chloro- 1 (pyrid-3-yl)-methyl- 511bromo- 1 (pyrid-3-yl)-methyl- 512 trifluoromethyl- 1(pyrid-3-yl)-methyl- 513 methyl- 2 (pyrid-3-yl)-methyl- 514 chloro- 2(pyrid-3-yl)-methyl- 515 bromo- 2 (pyrid-3-yl)-methyl- 516trifluoromethyl- 2 (pyrid-3-yl)-methyl- 517 methyl- 0(pyrid-4-yl)-methyl- 518 chloro- 0 (pyrid-4-yl)-methyl- 519 bromo- 0(pyrid-4-yl)-methyl- 520 trifluoromethyl- 0 (pyrid-4-yl)-methyl- 521methyl- 1 (pyrid-4-yl)-methyl- 522 chloro- 1 (pyrid-4-yl)-methyl- 523bromo- 1 (pyrid-4-yl)-methyl- 524 trifluoromethyl- 1(pyrid-4-yl)-methyl- 525 methyl- 2 (pyrid-4-yl)-methyl- 526 chloro- 2(pyrid-4-yl)-methyl- 527 bromo- 2 (pyrid-4-yl)-methyl- 528trifluoromethyl- 2 (pyrid-4-yl)-methyl- 529 methyl- 0 oxetan-3yl- 530chloro- 0 oxetan-3yl- 531 bromo- 0 oxetan-3yl- 532 trifluoromethyl- 0oxetan-3yl- 533 methyl- 1 oxetan-3yl- 534 chloro- 1 oxetan-3yl- 535bromo- 1 oxetan-3yl- 536 trifluoromethyl- 1 oxetan-3yl- 537 methyl- 2oxetan-3yl- 538 chloro- 2 oxetan-3yl- 539 bromo- 2 oxetan-3yl- 540trifluoromethyl- 2 oxetan-3yl- 541 methyl- 0 oxetan-3ylmethyl 542chloro- 0 oxetan-3ylmethyl 543 bromo- 0 oxetan-3ylmethyl 544trifluoromethyl- 0 oxetan-3ylmethyl 545 methyl- 1 oxetan-3ylmethyl 546chloro- 1 oxetan-3ylmethyl 547 bromo- 1 oxetan-3ylmethyl 548trifluoromethyl- 1 oxetan-3ylmethyl 549 methyl- 2 oxetan-3ylmethyl 550chloro- 2 oxetan-3ylmethyl 551 bromo- 2 oxetan-3ylmethyl 552trifluoromethyl- 2 oxetan-3ylmethyl 553 methyl- 0(tetrahydrofuran-2-yl)-methyl- 554 chloro- 0(tetrahydrofuran-2-yl)-methyl- 555 bromo- 0(tetrahydrofuran-2-yl)-methyl- 556 trifluoromethyl- 0(tetrahydrofuran-2-yl)-methyl- 557 methyl- 1(tetrahydrofuran-2-yl)-methyl- 558 chloro- 1(tetrahydrofuran-2-yl)-methyl- 559 bromo- 1(tetrahydrofuran-2-yl)-methyl- 560 trifluoromethyl- 1(tetrahydrofuran-2-yl)-methyl- 561 methyl- 2(tetrahydrofuran-2-yl)-methyl- 562 chloro- 2(tetrahydrofuran-2-yl)-methyl- 563 bromo- 2(tetrahydrofuran-2-yl)-methyl- 564 trifluoromethyl- 2(tetrahydrofuran-2-yl)-methyl- 565 methyl- 0(tetrahydrofuran-3-yl)-methyl- 566 chloro- 0(tetrahydrofuran-3-yl)-methyl- 567 bromo- 0(tetrahydrofuran-3-yl)-methyl- 568 trifluoromethyl- 0(tetrahydrofuran-3-yl)-methyl- 569 methyl- 1(tetrahydrofuran-3-yl)-methyl- 570 chloro- 1(tetrahydrofuran-3-yl)-methyl- 571 bromo- 1(tetrahydrofuran-3-yl)-methyl- 572 trifluoromethyl- 1(tetrahydrofuran-3-yl)-methyl- 573 methyl- 2(tetrahydrofuran-3-yl)-methyl- 574 chloro- 2(tetrahydrofuran-3-yl)-methyl- 575 bromo- 2(tetrahydrofuran-3-yl)-methyl- 576 trifluoromethyl- 2(tetrahydrofuran-3-yl)-methyl- 577 methyl- 0 (4-fluorophenyl)-methyl-578 chloro- 0 (4-fluorophenyl)-methyl- 579 bromo- 0(4-fluorophenyl)-methyl- 580 trifluoromethyl- 0 (4-fluorophenyl)-methyl-581 methyl- 1 (4-fluorophenyl)-methyl- 582 chloro- 1(4-fluorophenyl)-methyl- 583 bromo- 1 (4-fluorophenyl)-methyl- 584trifluoromethyl- 1 (4-fluorophenyl)-methyl- 585 methyl- 2(4-fluorophenyl)-methyl- 586 chloro- 2 (4-fluorophenyl)-methyl- 587bromo- 2 (4-fluorophenyl)-methyl- 588 trifluoromethyl- 2(4-fluorophenyl)-methyl- 589 methyl- 0 (4-chlorophenyl)-methyl- 590chloro- 0 (4-chlorophenyl)-methyl- 591 bromo- 0 (4-chlorophenyl)-methyl-592 trifluoromethyl- 0 (4-chlorophenyl)-methyl- 593 methyl- 1(4-chlorophenyl)-methyl- 594 chloro- 1 (4-chlorophenyl)-methyl- 595bromo- 1 (4-chlorophenyl)-methyl- 596 trifluoromethyl- 1(4-chlorophenyl)-methyl- 597 methyl- 2 (4-chlorophenyl)-methyl- 598chloro- 2 (4-chlorophenyl)-methyl- 599 bromo- 2 (4-chlorophenyl)-methyl-600 trifluoromethyl- 2 (4-chlorophenyl)-methyl- 601 methyl- 04-fluorophenyl- 602 chloro- 0 4-fluorophenyl- 603 bromo- 04-fluorophenyl- 604 trifluoromethyl- 0 4-fluorophenyl- 605 methyl- 14-fluorophenyl- 606 chloro- 1 4-fluorophenyl- 607 bromo- 14-fluorophenyl- 608 trifluoromethyl- 1 4-fluorophenyl- 609 methyl- 24-fluorophenyl- 610 chloro- 2 4-fluorophenyl- 611 bromo- 24-fluorophenyl- 612 trifluoromethyl- 2 4-fluorophenyl- 613 methyl- 04-chlorophenyl- 614 chloro- 0 4-chlorophenyl- 615 bromo- 04-chlorophenyl- 616 trifluoromethyl- 0 4-chlorophenyl- 617 methyl- 14-chlorophenyl- 618 chloro- 1 4-chlorophenyl- 619 bromo- 14-chlorophenyl- 620 trifluoromethyl- 1 4-chlorophenyl- 621 methyl- 24-chlorophenyl- 622 chloro- 2 4-chlorophenyl- 623 bromo- 24-chlorophenyl- 624 trifluoromethyl- 2 4-chlorophenyl- 625 methyl- 02-furylmethyl- 626 chloro- 0 2-furylmethyl- 627 bromo- 0 2-furylmethyl-628 trifluoromethyl- 0 2-furylmethyl- 629 methyl- 1 2-furylmethyl- 630chloro- 1 2-furylmethyl- 631 bromo- 1 2-furylmethyl- 632trifluoromethyl- 1 2-furylmethyl- 633 methyl- 2 2-furylmethyl- 634chloro- 2 2-furylmethyl- 635 bromo- 2 2-furylmethyl- 636trifluoromethyl- 2 2-furylmethyl- 637 methyl- 0(4-chloro-pyrid-2-yl)-methyl- 638 chloro- 0(4-chloro-pyrid-2-yl)-methyl- 639 bromo- 0 (4-chloro-pyrid-2-yl)-methyl-640 trifluoromethyl- 0 (4-chloro-pyrid-2-yl)-methyl- 641 methyl- 1(4-chloro-pyrid-2-yl)-methyl- 642 chloro- 1(4-chloro-pyrid-2-yl)-methyl- 643 bromo- 1 (4-chloro-pyrid-2-yl)-methyl-644 trifluoromethyl- 1 (4-chloro-pyrid-2-yl)-methyl- 645 methyl- 2(4-chloro-pyrid-2-yl)-methyl- 646 chloro- 2(4-chloro-pyrid-2-yl)-methyl- 647 bromo- 2 (4-chloro-pyrid-2-yl)-methyl-648 trifluoromethyl- 2 (4-chloro-pyrid-2-yl)-methyl- 649 methyl- 0(4-chloro-pyrid-3-yl)-methyl- 650 chloro- 0(4-chloro-pyrid-3-yl)-methyl- 651 bromo- 0 (4-chloro-pyrid-3-yl)-methyl-652 trifluoromethyl- 0 (4-chloro-pyrid-3-yl)-methyl- 653 methyl- 1(4-chloro-pyrid-3-yl)-methyl- 654 chloro- 1(4-chloro-pyrid-3-yl)-methyl- 655 bromo- 1 (4-chloro-pyrid-3-yl)-methyl-656 trifluoromethyl- 1 (4-chloro-pyrid-3-yl)-methyl- 657 methyl- 2(4-chloro-pyrid-3-yl)-methyl- 658 chloro- 2(4-chloro-pyrid-3-yl)-methyl- 659 bromo- 2 (4-chloro-pyrid-3-yl)-methyl-660 trifluoromethyl- 2 (4-chloro-pyrid-3-yl)-methyl- 661 methyl- 0(3-chloro-pyrid-4-yl)-methyl- 662 chloro- 0(3-chloro-pyrid-4-yl)-methyl- 663 bromo- 0 (3-chloro-pyrid-4-yl)-methyl-664 trifluoromethyl- 0 (3-chloro-pyrid-4-yl)-methyl- 665 methyl- 1(3-chloro-pyrid-4-yl)-methyl- 666 chloro- 1(3-chloro-pyrid-4-yl)-methyl- 667 bromo- 1 (3-chloro-pyrid-4-yl)-methyl-668 trifluoromethyl- 1 (3-chloro-pyrid-4-yl)-methyl- 669 methyl- 2(3-chloro-pyrid-4-yl)-methyl- 670 chloro- 2(3-chloro-pyrid-4-yl)-methyl- 671 bromo- 2 (3-chloro-pyrid-4-yl)-methyl-672 trifluoromethyl- 2 (3-chloro-pyrid-4-yl)-methyl- 673 methyl- 02-cyano-ethyl 674 chloro- 0 2-cyano-ethyl 675 bromo- 0 2-cyano-ethyl 676trifluoromethyl- 0 2-cyano-ethyl 677 methyl- 1 2-cyano-ethyl 678 chloro-1 2-cyano-ethyl 679 bromo- 1 2-cyano-ethyl 680 trifluoromethyl- 12-cyano-ethyl 681 methyl- 2 2-cyano-ethyl 682 chloro- 2 2-cyano-ethyl683 bromo- 2 2-cyano-ethyl 684 trifluoromethyl- 2 2-cyano-ethyl 685methyl- 0 2-methoxy-ethyl- 686 chloro- 0 2-methoxy-ethyl- 687 bromo- 02-methoxy-ethyl- 688 trifluoromethyl- 0 2-methoxy-ethyl- 689 methyl- 12-methoxy-ethyl- 690 chloro- 1 2-methoxy-ethyl- 691 bromo- 12-methoxy-ethyl- 692 trifluoromethyl- 1 2-methoxy-ethyl- 693 methyl- 22-methoxy-ethyl- 694 chloro- 2 2-methoxy-ethyl- 695 bromo- 22-methoxy-ethyl- 696 trifluoromethyl- 2 2-methoxy-ethyl- 697 methyl- 01-methylthio-prop-2-yl- 698 chloro- 0 1-methylthio-prop-2-yl- 699 bromo-0 1-methylthio-prop-2-yl- 700 trifluoromethyl- 0 1-methylthio-prop-2-yl-701 methyl- 1 1-methylthio-prop-2-yl- 702 chloro- 11-methylthio-prop-2-yl- 703 bromo- 1 1-methylthio-prop-2-yl- 704trifluoromethyl- 1 1-methylthio-prop-2-yl- 705 methyl- 21-methylthio-prop-2-yl- 706 chloro- 2 1-methylthio-prop-2-yl- 707 bromo-2 1-methylthio-prop-2-yl- 708 trifluoromethyl- 2 1-methylthio-prop-2-yl-709 methyl- 0 2-methylthio-ethyl- 710 chloro- 0 2-methylthio-ethyl- 711bromo- 0 2-methylthio-ethyl- 712 trifluoromethyl- 0 2-methylthio-ethyl-713 methyl- 1 2-methylthio-ethyl- 714 chloro- 1 2-methylthio-ethyl- 715bromo- 1 2-methylthio-ethyl- 716 trifluoromethyl- 1 2-methylthio-ethyl-717 methyl- 2 2-methylthio-ethyl- 718 chloro- 2 2-methylthio-ethyl- 719bromo- 2 2-methylthio-ethyl- 720 trifluoromethyl- 2 2-methylthio-ethyl-

Table 1

-   Table 1 provides 720 compounds of formula IA wherein R1 is hydrogen,    R3 is trifluoromethyl-, R4 is 3,5-dichlorophenyl-, Y1-Y2-Y3 is    —C═N—O—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 2-   Table 2 provides 720 compounds of formula IA wherein R1 is methyl-,    R3 is trifluoromethyl-, R4 is 3,5-dichlorophenyl-, Y1-Y2-Y3 is    —C═N—O—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 3-   Table 3 provides 720 compounds of formula IA wherein R1 is ethyl-,    R3 is trifluoromethyl-, R4 is 3,5-dichlorophenyl-, Y1-Y2-Y3 is    —C═N—O—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 4-   Table 4 provides 720 compounds of formula IA wherein R1 is hydrogen,    R3 is dichloromethyl-, R4 is 3,5-dichlorophenyl-, Y1-Y2-Y3 is    —C═N—O—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 5-   Table 5 provides 720 compounds of formula IA wherein R1 is methyl-,    R3 is dichloromethyl-, R4 is 3,5-dichlorophenyl-, Y1-Y2-Y3 is    —C═N—O—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 6-   Table 6 provides 720 compounds of formula IA wherein R1 is ethyl-,    R3 is dichloromethyl-, R4 is 3,5-dichlorophenyl-, Y1-Y2-Y3 is    —C═N—O—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 7-   Table 7 provides 720 compounds of formula IA wherein R1 is hydrogen,    R3 is trifluoromethyl-, R4 is 3,4-dichlorophenyl-, Y1-Y2-Y3 is    —C═N—O—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 8-   Table 8 provides 720 compounds of formula IA wherein R1 is methyl-,    R3 is trifluoromethyl-, R4 is 3,4-dichlorophenyl-, Y1-Y2-Y3 is    —C═N—O—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 9-   Table 9 provides 720 compounds of formula IA wherein R1 is ethyl-,    R3 is trifluoromethyl-, R4 is 3,4-dichlorophenyl-, Y1-Y2-Y3 is    —C═N—O—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 10-   Table 10 provides 720 compounds of formula IA wherein R1 is    hydrogen, R3 is dichloromethyl-, R4 is 3,4-dichlorophenyl-, Y1-Y2-Y3    is —C═N—O—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 11-   Table 11 provides 720 compounds of formula IA wherein R1 is methyl-,    R3 is dichloromethyl-, R4 is 3,4-dichlorophenyl-, Y1-Y2-Y3 is    —C═N—O—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 12-   Table 12 provides 720 compounds of formula IA wherein R1 is ethyl-,    R3 is dichloromethyl-, R4 is 3,4-dichlorophenyl-, Y1-Y2-Y3 is    —C═N—O—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 13-   Table 13 provides 720 compounds of formula IA wherein R1 is    hydrogen, R3 is trifluoromethyl-, R4 is    3,5-dichloro-4-fluorophenyl-, Y1-Y2-Y3 is —C═N—O—, A2 is CH, A3 is    CH, A4 is CH, and R5b, n and R2 are as defined in Table P.    Table 14-   Table 14 provides 720 compounds of formula IA wherein R1 is methyl-,    R3 is trifluoromethyl-, R4 is 3,5-dichloro-4-fluorophenyl-, Y1-Y2-Y3    is —C═N—O—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 15-   Table 15 provides 720 compounds of formula IA wherein R1 is ethyl-,    R3 is trifluoromethyl-, R4 is 3,5-dichloro-4-fluorophenyl-, Y1-Y2-Y3    is —C═N—O—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 16-   Table 16 provides 720 compounds of formula IA wherein R1 is    hydrogen, R3 is dichloromethyl-, R4 is 3,5-dichloro-4-fluorophenyl-,    Y1-Y2-Y3 is —C═N—O—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2    are as defined in Table P.    Table 17-   Table 17 provides 720 compounds of formula IA wherein R1 is methyl-,    R3 is dichloromethyl-, R4 is 3,5-dichloro-4-fluorophenyl-, Y1-Y2-Y3    is —C═N—O—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 18-   Table 18 provides 720 compounds of formula IA wherein R1 is ethyl-,    R3 is dichloromethyl-, R4 is 3,5-dichloro-4-fluorophenyl-, Y1-Y2-Y3    is —C═N—O—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 19-   Table 19 provides 720 compounds of formula IA wherein R1 is    hydrogen, R3 is trifluoromethyl-, R4 is 3,4,5-trichlorophenyl-,    Y1-Y2-Y3 is —C═N—O—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2    are as defined in Table P.    Table 20-   Table 20 provides 720 compounds of formula IA wherein R1 is methyl-,    R3 is trifluoromethyl-, R4 is 3,4,5-trichlorophenyl-, Y1-Y2-Y3 is    —C═N—O—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 21-   Table 21 provides 720 compounds of formula IA wherein R1 is ethyl-,    R3 is trifluoromethyl-, R4 is 3,4,5-trichlorophenyl-, Y1-Y2-Y3 is    —C═N—O—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 22-   Table 22 provides 720 compounds of formula IA wherein R1 is    hydrogen, R3 is dichloromethyl-, R4 is 3,4,5-trichlorophenyl-,    Y1-Y2-Y3 is —C═N—O—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2    are as defined in Table P.    Table 23-   Table 23 provides 720 compounds of formula IA wherein R1 is methyl-,    R3 is dichloromethyl-, R4 is 3,4,5-trichlorophenyl-, Y1-Y2-Y3 is    —C═N—O—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 24-   Table 24 provides 720 compounds of formula IA wherein R1 is ethyl-,    R3 is dichloromethyl-, R4 is 3,4,5-trichlorophenyl-, Y1-Y2-Y3 is    —C═N—O—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 25-   Table 25 provides 720 compounds of formula IA wherein R1 is    hydrogen, R3 is trifluoromethyl-, R4 is 3-chloro-5-fluorophenyl-,    Y1-Y2-Y3 is —C═N—O—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2    are as defined in Table P.    Table 26-   Table 26 provides 720 compounds of formula IA wherein R1 is methyl-,    R3 is trifluoromethyl-, R4 is 3-chloro-5-fluorophenyl-, Y1-Y2-Y3 is    —C═N—O—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 27-   Table 27 provides 720 compounds of formula IA wherein R1 is ethyl-,    R3 is trifluoromethyl-, R4 is 3-chloro-5-fluorophenyl-, Y1-Y2-Y3 is    —C═N—O—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 28-   Table 28 provides 720 compounds of formula IA wherein R1 is    hydrogen, R3 is dichloromethyl-, R4 is 3-chloro-5-fluorophenyl-,    Y1-Y2-Y3 is —C═N—O—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2    are as defined in Table P.    Table 29-   Table 29 provides 720 compounds of formula IA wherein R1 is methyl-,    R3 is dichloromethyl-, R4 is 3-chloro-5-fluorophenyl-, Y1-Y2-Y3 is    —C═N—O—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 30-   Table 30 provides 720 compounds of formula IA wherein R1 is ethyl-,    R3 is dichloromethyl-, R4 is 3-chloro-5-fluorophenyl-, Y1-Y2-Y3 is    —C═N—O—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 31-   Table 31 provides 720 compounds of formula IA wherein R1 is    hydrogen, R3 is trifluoromethyl-, R4 is    3-chloro-5-(trifluoromethyl)phenyl-, Y1-Y2-Y3 is —C═N—O—, A2 is CH,    A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.    Table 32-   Table 32 provides 720 compounds of formula IA wherein R1 is methyl-,    R3 is trifluoromethyl-, R4 is 3-chloro-5-(trifluoromethyl)phenyl-,    Y1-Y2-Y3 is —C═N—O—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2    are as defined in Table P.    Table 33-   Table 33 provides 720 compounds of formula IA wherein R1 is ethyl-,    R3 is trifluoromethyl-, R4 is 3-chloro-5-(trifluoromethyl)phenyl-,    Y1-Y2-Y3 is —C═N—O—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2    are as defined in Table P.    Table 34-   Table 34 provides 720 compounds of formula IA wherein R1 is    hydrogen, R3 is dichloromethyl-, R4 is    3-chloro-5-(trifluoromethyl)phenyl-, Y1-Y2-Y3 is —C═N—O—, A2 is CH,    A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.    Table 35-   Table 35 provides 720 compounds of formula IA wherein R1 is methyl-,    R3 is dichloromethyl-, R4 is 3-chloro-5-(trifluoromethyl)phenyl-,    Y1-Y2-Y3 is —C═N—O—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2    are as defined in Table P.    Table 36-   Table 36 provides 720 compounds of formula IA wherein R1 is ethyl-,    R3 is dichloromethyl-, R4 is 3-chloro-5-(trifluoromethyl)phenyl-,    Y1-Y2-Y3 is —C═N—O—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2    are as defined in Table P.    Table 37-   Table 37 provides 720 compounds of formula IA wherein R1 is    hydrogen, R3 is trifluoromethyl-, R4 is    3,5-bis(trifluoromethyl)phenyl-, Y1-Y2-Y3 is —C═N—O—, A2 is CH, A3    is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.    Table 38-   Table 38 provides 720 compounds of formula IA wherein R1 is methyl-,    R3 is trifluoromethyl-, R4 is 3,5-bis(trifluoromethyl)phenyl-,    Y1-Y2-Y3 is —C═N—O—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2    are as defined in Table P.    Table 39-   Table 39 provides 720 compounds of formula IA wherein R1 is ethyl-,    R3 is trifluoromethyl-, R4 is 3,5-bis(trifluromethyl)phenyl-,    Y1-Y2-Y3 is —C═N—O—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2    are as defined in Table P.    Table 40-   Table 40 provides 720 compounds of formula IA wherein R1 is    hydrogen, R3 is dichloromethyl-, R4 is    3,5-bis(trifluoromethyl)phenyl-, Y1-Y2-Y3 is —C═N—O—, A2 is CH, A3    is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.    Table 41-   Table 41 provides 720 compounds of formula IA wherein R1 is methyl-,    R3 is dichloromethyl-, R4 is 3,5-bis(trifluoromethyl)phenyl-,    Y1-Y2-Y3 is —C═N—O—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2    are as defined in Table P.    Table 42-   Table 42 provides 720 compounds of formula IA wherein R1 is ethyl-,    R3 is dichloromethyl-, R4 is 3,5-bis(trifluoromethyl)phenyl-,    Y1-Y2-Y3 is —C═N—O—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2    are as defined in Table P.    Table 43-   Table 43 provides 720 compounds of formula IA wherein R1 is    hydrogen, R3 is trifluoromethyl-, R4 is 3-(trifluoromethyl)phenyl-,    Y1-Y2-Y3 is —C═N—O—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2    are as defined in Table P.    Table 44-   Table 44 provides 720 compounds of formula IA wherein R1 is methyl-,    R3 is trifluoromethyl-, R4 is 3-(trifluoromethyl)phenyl-, Y1-Y2-Y3    is —C═N—O—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 45-   Table 45 provides 720 compounds of formula IA wherein R1 is ethyl-,    R3 is trifluoromethyl-, R4 is 3-(trifluoromethyl)phenyl-, Y1-Y2-Y3    is —C═N—O—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 46-   Table 46 provides 720 compounds of formula IA wherein R1 is    hydrogen, R3 is dichloromethyl-, R4 is 3-(trifluoromethyl)phenyl-,    Y1-Y2-Y3 is —C═N—O—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2    are as defined in Table P.    Table 47-   Table 47 provides 720 compounds of formula IA wherein R1 is methyl-,    R3 is dichloromethyl-, R4 is 3-(trifluoromethyl)phenyl-, Y1-Y2-Y3 is    —C═N—O—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 48-   Table 48 provides 720 compounds of formula IA wherein R1 is ethyl-,    R3 is dichloromethyl-, R4 is 3-(trifluoromethyl)phenyl-, Y1-Y2-Y3 is    —C═N—O—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 49-   Table 49 provides 720 compounds of formula IA wherein R1 is    hydrogen, R3 is trifluoromethyl-, R4 is 3,5-dichlorophenyl-,    Y1-Y2-Y3 is —C═N—CH2—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and    R2 are as defined in Table P.    Table 50-   Table 50 provides 720 compounds of formula IA wherein R1 is methyl-,    R3 is trifluoromethyl-, R4 is 3,5-dichlorophenyl-, Y1-Y2-Y3 is    —C═N—CH2-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 51-   Table 51 provides 720 compounds of formula IA wherein R1 is ethyl-,    R3 is trifluoromethyl-, R4 is 3,5-dichlorophenyl-, Y1-Y2-Y3 is    —C═N—CH2-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 52-   Table 52 provides 720 compounds of formula IA wherein R1 is    hydrogen, R3 is dichloromethyl-, R4 is 3,5-dichlorophenyl-, Y1-Y2-Y3    is —C═N—CH2-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 53-   Table 53 provides 720 compounds of formula IA wherein R1 is methyl-,    R3 is dichloromethyl-, R4 is 3,5-dichlorophenyl-, Y1-Y2-Y3 is    —C═N—CH2-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 54-   Table 54 provides 720 compounds of formula IA wherein R1 is ethyl-,    R3 is dichloromethyl-, R4 is 3,5-dichlorophenyl-, Y1-Y2-Y3 is    —C═N—CH2-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 55-   Table 55 provides 720 compounds of formula IA wherein R1 is    hydrogen, R3 is trifluoromethyl-, R4 is 3,4-dichlorophenyl-,    Y1-Y2-Y3 is —C═N—CH2-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and    R2 are as defined in Table P.    Table 56-   Table 56 provides 720 compounds of formula IA wherein R1 is methyl-,    R3 is trifluoromethyl-, R4 is 3,4-dichlorophenyl-, Y1-Y2-Y3 is    —C═N—CH2-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 57-   Table 57 provides 720 compounds of formula IA wherein R1 is ethyl-,    R3 is trifluoromethyl-, R4 is 3,4-dichlorophenyl-, Y1-Y2-Y3 is    —C═N—CH2-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 58-   Table 58 provides 720 compounds of formula IA wherein R1 is    hydrogen, R3 is dichloromethyl-, R4 is 3,4-dichlorophenyl-, Y1-Y2-Y3    is —C═N—CH2-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 59-   Table 59 provides 720 compounds of formula IA wherein R1 is methyl-,    R3 is dichloromethyl-, R4 is 3,4-dichlorophenyl-, Y1-Y2-Y3 is    —C═N—CH2-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 60-   Table 60 provides 720 compounds of formula IA wherein R1 is ethyl-,    R3 is dichloromethyl-, R4 is 3,4-dichlorophenyl-, Y1-Y2-Y3 is    —C═N—CH2-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 61-   Table 61 provides 720 compounds of formula IA wherein R1 is    hydrogen, R3 is trifluoromethyl-, R4 is    3,5-dichloro-4-fluorophenyl-, Y1-Y2-Y3 is —C═N—CH2-, A2 is CH, A3 is    CH, A4 is CH, and R5b, n and R2 are as defined in Table P.    Table 62-   Table 62 provides 720 compounds of formula IA wherein R1 is methyl-,    R3 is trifluoromethyl-, R4 is 3,5-dichloro-4-fluorophenyl-, Y1-Y2-Y3    is —C═N—CH2-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 63-   Table 63 provides 720 compounds of formula IA wherein R1 is ethyl-,    R3 is trifluoromethyl-, R4 is 3,5-dichloro-4-fluorophenyl-, Y1-Y2-Y3    is —C═N—CH2-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 64-   Table 64 provides 720 compounds of formula IA wherein R1 is    hydrogen, R3 is dichloromethyl-, R4 is 3,5-dichloro-4-fluorophenyl-,    Y1-Y2-Y3 is —C═N—CH2-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and    R2 are as defined in Table P.    Table 65-   Table 65 provides 720 compounds of formula IA wherein R1 is methyl-,    R3 is dichloromethyl-, R4 is 3,5-dichloro-4-fluorophenyl-, Y1-Y2-Y3    is —C═N—CH2-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 66-   Table 66 provides 720 compounds of formula IA wherein R1 is ethyl-,    R3 is dichloromethyl-, R4 is 3,5-dichloro-4-fluorophenyl-, Y1-Y2-Y3    is —C═N—CH2-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 67-   Table 67 provides 720 compounds of formula IA wherein R1 is    hydrogen, R3 is trifluoromethyl-, R4 is 3,4,5-trichlorophenyl-,    Y1-Y2-Y3 is —C═N—CH2-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and    R2 are as defined in Table P.    Table 68-   Table 68 provides 720 compounds of formula IA wherein R1 is methyl-,    R3 is trifluoromethyl-, R4 is 3,4,5-trichlorophenyl-, Y1-Y2-Y3 is    —C═N—CH2-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 69-   Table 69 provides 720 compounds of formula IA wherein R1 is ethyl-,    R3 is trifluoromethyl-, R4 is 3,4,5-trichlorophenyl-, Y1-Y2-Y3 is    —C═N—CH2-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 70-   Table 70 provides 720 compounds of formula IA wherein R1 is    hydrogen, R3 is dichloromethyl-, R4 is 3,4,5-trichlorophenyl-,    Y1-Y2-Y3 is —C═N—CH2-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and    R2 are as defined in Table P.    Table 71-   Table 71 provides 720 compounds of formula IA wherein R1 is methyl-,    R3 is dichloromethyl-, R4 is 3,4,5-trichlorophenyl-, Y1-Y2-Y3 is    —C═N—CH2-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 72-   Table 72 provides 720 compounds of formula IA wherein R1 is ethyl-,    R3 is dichloromethyl-, R4 is 3,4,5-trichlorophenyl-, Y1-Y2-Y3 is    —C═N—CH2-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 73-   Table 73 provides 720 compounds of formula IA wherein R1 is    hydrogen, R3 is trifluoromethyl-, R4 is 3-chloro-5-fluorophenyl-,    Y1-Y2-Y3 is —C═N—CH2-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and    R2 are as defined in Table P.    Table 74-   Table 74 provides 720 compounds of formula IA wherein R1 is methyl-,    R3 is trifluoromethyl-, R4 is 3-chloro-5-fluorophenyl-, Y1-Y2-Y3 is    —C═N—CH2-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 75-   Table 75 provides 720 compounds of formula IA wherein R1 is ethyl-,    R3 is trifluoromethyl-, R4 is 3-chloro-5-fluorophenyl-, Y1-Y2-Y3 is    —C═N—CH2-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 76-   Table 76 provides 720 compounds of formula IA wherein R1 is    hydrogen, R3 is dichloromethyl-, R4 is 3-chloro-5-fluorophenyl-,    Y1-Y2-Y3 is —C═N—CH2-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and    R2 are as defined in Table P.    Table 77-   Table 77 provides 720 compounds of formula IA wherein R1 is methyl-,    R3 is dichloromethyl-, R4 is 3-chloro-5-fluorophenyl-, Y1-Y2-Y3 is    —C═N—CH2-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 78-   Table 78 provides 720 compounds of formula IA wherein R1 is ethyl-,    R3 is dichloromethyl-, R4 is 3-chloro-5-fluorophenyl-, Y1-Y2-Y3 is    —C═N—CH2-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 79-   Table 79 provides 720 compounds of formula IA wherein R1 is    hydrogen, R3 is trifluoromethyl-, R4 is    3-chloro-5-(trifluoromethyl)phenyl-, Y1-Y2-Y3 is —C═N—CH2-, A2 is    CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.    Table 80-   Table 80 provides 720 compounds of formula IA wherein R1 is methyl-,    R3 is trifluoromethyl-, R4 is 3-chloro-5-(trifluoromethyl)phenyl-,    Y1-Y2-Y3 is —C═N—CH2-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and    R2 are as defined in Table P.    Table 81-   Table 81 provides 720 compounds of formula IA wherein R1 is ethyl-,    R3 is trifluoromethyl-, R4 is 3-chloro-5-(trifluoromethyl)phenyl-,    Y1-Y2-Y3 is —C═N—CH2-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and    R2 are as defined in Table P.    Table 82-   Table 82 provides 720 compounds of formula IA wherein R1 is    hydrogen, R3 is dichloromethyl-, R4 is    3-chloro-5-(trifluoromethyl)phenyl-, Y1-Y2-Y3 is —C═N—CH2-, A2 is    CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.    Table 83-   Table 83 provides 720 compounds of formula IA wherein R1 is methyl-,    R3 is dichloromethyl-, R4 is 3-chloro-5-(trifluoromethyl)phenyl-,    Y1-Y2-Y3 is —C═N—CH2-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and    R2 are as defined in Table P.    Table 84-   Table 84 provides 720 compounds of formula IA wherein R1 is ethyl-,    R3 is dichloromethyl-, R4 is 3-chloro-5-(trifluoromethyl)phenyl-,    Y1-Y2-Y3 is —C═N—CH2-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and    R2 are as defined in Table P.    Table 85-   Table 85 provides 720 compounds of formula IA wherein R1 is    hydrogen, R3 is trifluoromethyl-, R4 is    3,5-bis(trifluoromethyl)phenyl-, Y1-Y2-Y3 is —C═N—CH2-, A2 is CH, A3    is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.    Table 86-   Table 86 provides 720 compounds of formula IA wherein R1 is methyl-,    R3 is trifluoromethyl-, R4 is 3,5-bis(trifluoromethyl)phenyl-,    Y1-Y2-Y3 is —C═N—CH2-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and    R2 are as defined in Table P.    Table 87-   Table 87 provides 720 compounds of formula IA wherein R1 is ethyl-,    R3 is trifluoromethyl-, R4 is 3,5-bis(trifluoromethyl)phenyl-,    Y1-Y2-Y3 is —C═N—CH2-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and    R2 are as defined in Table P.    Table 88-   Table 88 provides 720 compounds of formula IA wherein R1 is    hydrogen, R3 is dichloromethyl-, R4 is    3,5-bis(trifluoromethyl)phenyl-, Y1-Y2-Y3 is —C═N—CH2-, A2 is CH, A3    is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.    Table 89-   Table 89 provides 720 compounds of formula IA wherein R1 is methyl-,    R3 is dichloromethyl-, R4 is 3,5-bis(trifluoromethyl)phenyl-,    Y1-Y2-Y3 is —C═N—CH2-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and    R2 are as defined in Table P.    Table 90-   Table 90 provides 720 compounds of formula IA wherein R1 is ethyl-,    R3 is dichloromethyl-, R4 is 3,5-bis(trifluoromethyl)phenyl-,    Y1-Y2-Y3 is —C═N—CH2-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and    R2 are as defined in Table P.    Table 91-   Table 91 provides 720 compounds of formula IA wherein R1 is    hydrogen, R3 is trifluoromethyl-, R4 is 3-(trifluoromethyl)phenyl-,    Y1-Y2-Y3 is —C═N—CH2-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and    R2 are as defined in Table P.    Table 92-   Table 92 provides 720 compounds of formula IA wherein R1 is methyl-,    R3 is trifluoromethyl-, R4 is 3-(trifluoromethyl)phenyl-, Y1-Y2-Y3    is —C═N—CH2-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 93-   Table 93 provides 720 compounds of formula IA wherein R1 is ethyl-,    R3 is trifluoromethyl-, R4 is 3-(trifluoromethyl)phenyl-, Y1-Y2-Y3    is —C═N—CH2-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 94-   Table 94 provides 720 compounds of formula IA wherein R1 is    hydrogen, R3 is dichloromethyl-, R4 is 3-(trifluoromethyl)phenyl-,    Y1-Y2-Y3 is —C═N—CH2-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and    R2 are as defined in Table P.    Table 95-   Table 95 provides 720 compounds of formula IA wherein R1 is methyl-,    R3 is dichloromethyl-, R4 is 3-(trifluoromethyl)phenyl-, Y1-Y2-Y3 is    —C═N—CH2-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 96-   Table 96 provides 720 compounds of formula IA wherein R1 is ethyl-,    R3 is dichloromethyl-, R4 is 3-(trifluoromethyl)phenyl-, Y1-Y2-Y3 is    —C═N—CH2-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 97-   Table 97 provides 720 compounds of formula IA wherein R1 is    hydrogen, R3 is trifluoromethyl-, R4 is 3,5-dichlorophenyl-,    Y1-Y2-Y3 is —N—CH2-CH2-, A2 is CH, A3 is CH, A4 is CH, and R5b, n    and R2 are as defined in Table P.    Table 98-   Table 98 provides 720 compounds of formula IA wherein R1 is methyl-,    R3 is trifluoromethyl-, R4 is 3,5-dichlorophenyl-, Y1-Y2-Y3 is    —N—CH2-CH2-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 99-   Table 99 provides 720 compounds of formula IA wherein R1 is ethyl-,    R3 is trifluoromethyl-, R4 is 3,5-dichlorophenyl-, Y1-Y2-Y3 is    —N—CH2-CH2-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 100-   Table 100 provides 720 compounds of formula IA wherein R1 is    hydrogen, R3 is dichloromethyl-, R4 is 3,5-dichlorophenyl-, Y1-Y2-Y3    is —N—CH2-CH2-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are    as defined in Table P.    Table 101-   Table 101 provides 720 compounds of formula IA wherein R1 is    methyl-, R3 is dichloromethyl-, R4 is 3,5-dichlorophenyl-, Y1-Y2-Y3    is —N—CH2-CH2-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are    as defined in Table P.    Table 102-   Table 102 provides 720 compounds of formula IA wherein R1 is ethyl-,    R3 is dichloromethyl-, R4 is 3,5-dichlorophenyl-, Y1-Y2-Y3 is    —N—CH2-CH2-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 103-   Table 103 provides 720 compounds of formula IA wherein R1 is    hydrogen, R3 is trifluoromethyl-, R4 is 3,4-dichlorophenyl-,    Y1-Y2-Y3 is —N—CH2-CH2-, A2 is CH, A3 is CH, A4 is CH, and R5b, n    and R2 are as defined in Table P.    Table 104-   Table 104 provides 720 compounds of formula IA wherein R1 is    methyl-, R3 is trifluoromethyl-, R4 is 3,4-dichlorophenyl-, Y1-Y2-Y3    is —N—CH2-CH2-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are    as defined in Table P.    Table 105-   Table 105 provides 720 compounds of formula IA wherein R1 is ethyl-,    R3 is trifluoromethyl-, R4 is 3,4-dichlorophenyl-, Y1-Y2-Y3 is    —N—CH2-CH2-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 106-   Table 106 provides 720 compounds of formula IA wherein R1 is    hydrogen, R3 is dichloromethyl-, R4 is 3,4-dichlorophenyl-, Y1-Y2-Y3    is —N—CH2-CH2-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are    as defined in Table P.    Table 107-   Table 107 provides 720 compounds of formula IA wherein R1 is    methyl-, R3 is dichloromethyl-, R4 is 3,4-dichlorophenyl-, Y1-Y2-Y3    is —N—CH2-CH2-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are    as defined in Table P.    Table 108-   Table 108 provides 720 compounds of formula IA wherein R1 is ethyl-,    R3 is dichloromethyl-, R4 is 3,4-dichlorophenyl-, Y1-Y2-Y3 is    —N—CH2-CH2-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 109-   Table 109 provides 720 compounds of formula IA wherein R1 is    hydrogen, R3 is trifluoromethyl-, R4 is    3,5-dichloro-4-fluorophenyl-, Y1-Y2-Y3 is —N—CH2-CH2-, A2 is CH, A3    is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.    Table 110-   Table 110 provides 720 compounds of formula IA wherein R1 is    methyl-, R3 is trifluoromethyl-, R4 is 3,5-dichloro-4-fluorophenyl-,    Y1-Y2-Y3 is —N—CH2-CH2-, A2 is CH, A3 is CH, A4 is CH, and R5b, n    and R2 are as defined in Table P.    Table 111-   Table 111 provides 720 compounds of formula IA wherein R1 is ethyl-,    R3 is trifluoromethyl-, R4 is 3,5-dichloro-4-fluorophenyl-, Y1-Y2-Y3    is —N—CH2-CH2-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are    as defined in Table P.    Table 112-   Table 112 provides 720 compounds of formula IA wherein R1 is    hydrogen, R3 is dichloromethyl-, R4 is 3,5-dichloro-4-fluorophenyl-,    Y1-Y2-Y3 is —N—CH2-CH2-, A2 is CH, A3 is CH, A4 is CH, and R5b, n    and R2 are as defined in Table P.    Table 113-   Table 113 provides 720 compounds of formula IA wherein R1 is    methyl-, R3 is dichloromethyl-, R4 is 3,5-dichloro-4-fluorophenyl-,    Y1-Y2-Y3 is —N—CH2-CH2-, A2 is CH, A3 is CH, A4 is CH, and R5b, n    and R2 are as defined in Table P.    Table 114-   Table 114 provides 720 compounds of formula IA wherein R1 is ethyl-,    R3 is dichloromethyl-, R4 is 3,5-dichloro-4-fluorophenyl-, Y1-Y2-Y3    is —N—CH2-CH2-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are    as defined in Table P.    Table 115-   Table 115 provides 720 compounds of formula IA wherein R1 is    hydrogen, R3 is trifluoromethyl-, R4 is 3,4,5-trichlorophenyl-,    Y1-Y2-Y3 is —N—CH2-CH2-, A2 is CH, A3 is CH, A4 is CH, and R5b, n    and R2 are as defined in Table P.    Table 116-   Table 116 provides 720 compounds of formula IA wherein R1 is    methyl-, R3 is trifluoromethyl-, R4 is 3,4,5-trichlorophenyl-,    Y1-Y2-Y3 is —N—CH2-CH2-, A2 is CH, A3 is CH, A4 is CH, and R5b, n    and R2 are as defined in Table P.    Table 117-   Table 117 provides 720 compounds of formula IA wherein R1 is ethyl-,    R3 is trifluoromethyl-, R4 is 3,4,5-trichlorophenyl-, Y1-Y2-Y3 is    —N—CH2-CH2-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 118-   Table 118 provides 720 compounds of formula IA wherein R1 is    hydrogen, R3 is dichloromethyl-, R4 is 3,4,5-trichlorophenyl-,    Y1-Y2-Y3 is —N—CH2-CH2-, A2 is CH, A3 is CH, A4 is CH, and R5b, n    and R2 are as defined in Table P.    Table 119-   Table 119 provides 720 compounds of formula IA wherein R1 is    methyl-, R3 is dichloromethyl-, R4 is 3,4,5-trichlorophenyl-,    Y1-Y2-Y3 is —N—CH2-CH2-, A2 is CH, A3 is CH, A4 is CH, and R5b, n    and R2 are as defined in Table P.    Table 120-   Table 120 provides 720 compounds of formula IA wherein R1 is ethyl-,    R3 is dichloromethyl-, R4 is 3,4,5-trichlorophenyl-, Y1-Y2-Y3 is    —N—CH2-CH2-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 121-   Table 121 provides 720 compounds of formula IA wherein R1 is    hydrogen, R3 is trifluoromethyl-, R4 is 3-chloro-5-fluorophenyl-,    Y1-Y2-Y3 is —N—CH2-CH2-, A2 is CH, A3 is CH, A4 is CH, and R5b, n    and R2 are as defined in Table P.    Table 122-   Table 122 provides 720 compounds of formula IA wherein R1 is    methyl-, R3 is trifluoromethyl-, R4 is 3-chloro-5-fluorophenyl-,    Y1-Y2-Y3 is —N—CH2-CH2-, A2 is CH, A3 is CH, A4 is CH, and R5b, n    and R2 are as defined in Table P.    Table 123-   Table 123 provides 720 compounds of formula IA wherein R1 is ethyl-,    R3 is trifluoromethyl-, R4 is 3-chloro-5-fluorophenyl-, Y1-Y2-Y3 is    —N—CH2-CH2-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 124-   Table 124 provides 720 compounds of formula IA wherein R1 is    hydrogen, R3 is dichloromethyl-, R4 is 3-chloro-5-fluorophenyl-,    Y1-Y2-Y3 is —N—CH2-CH2-, A2 is CH, A3 is CH, A4 is CH, and R5b, n    and R2 are as defined in Table P.    Table 125-   Table 125 provides 720 compounds of formula IA wherein R1 is    methyl-, R3 is dichloromethyl-, R4 is 3-chloro-5-fluorophenyl-,    Y1-Y2-Y3 is —N—CH2-CH2-, A2 is CH, A3 is CH, A4 is CH, and R5b, n    and R2 are as defined in Table P.    Table 126-   Table 126 provides 720 compounds of formula IA wherein R1 is ethyl-,    R3 is dichloromethyl-, R4 is 3-chloro-5-fluorophenyl-, Y1-Y2-Y3 is    —N—CH2-CH2-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 127-   Table 127 provides 720 compounds of formula IA wherein R1 is    hydrogen, R3 is trifluoromethyl-, R4 is    3-chloro-5-(trifluoromethyl)phenyl-, Y1-Y2-Y3 is —N—CH2-CH2-, A2 is    CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.    Table 128-   Table 128 provides 720 compounds of formula IA wherein R1 is    methyl-, R3 is trifluoromethyl-, R4 is    3-chloro-5-(trifluoromethyl)phenyl-, Y1-Y2-Y3 is —N—CH2-CH2-, A2 is    CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.    Table 129-   Table 129 provides 720 compounds of formula IA wherein R1 is ethyl-,    R3 is trifluoromethyl-, R4 is 3-chloro-5-(trifluoromethyl)phenyl-,    Y1-Y2-Y3 is —N—CH2-CH2-, A2 is CH, A3 is CH, A4 is CH, and R5b, n    and R2 are as defined in Table P.    Table 130-   Table 130 provides 720 compounds of formula IA wherein R1 is    hydrogen, R3 is dichloromethyl-, R4 is    3-chloro-5-(trifluoromethyl)phenyl-, Y1-Y2-Y3 is —N—CH2-CH2-, A2 is    CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.    Table 131-   Table 131 provides 720 compounds of formula IA wherein R1 is    methyl-, R3 is dichloromethyl-, R4 is    3-chloro-5-(trifluoromethyl)phenyl-, Y1-Y2-Y3 is —N—CH2-CH2-, A2 is    CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.    Table 132-   Table 132 provides 720 compounds of formula IA wherein R1 is ethyl-,    R3 is dichloromethyl-, R4 is 3-chloro-5-(trifluoromethyl)phenyl-,    Y1-Y2-Y3 is —N—CH2-CH2-, A2 is CH, A3 is CH, A4 is CH, and R5b, n    and R2 are as defined in Table P.    Table 133-   Table 133 provides 720 compounds of formula IA wherein R1 is    hydrogen, R3 is trifluoromethyl-, R4 is    3,5-bis(trifluoromethyl)phenyl-, Y1-Y2-Y3 is —N—CH2-CH2-, A2 is CH,    A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.    Table 134-   Table 134 provides 720 compounds of formula IA wherein R1 is    methyl-, R3 is trifluoromethyl-, R4 is    3,5-bis(trifluoromethyl)phenyl-, Y1-Y2-Y3 is —N—CH2-CH2-, A2 is CH,    A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.    Table 135-   Table 135 provides 720 compounds of formula IA wherein R1 is ethyl-,    R3 is trifluoromethyl-, R4 is 3,5-bis(trifluoromethyl)phenyl-,    Y1-Y2-Y3 is —N—CH2-CH2-, A2 is CH, A3 is CH, A4 is CH, and R5b, n    and R2 are as defined in Table P.    Table 136-   Table 136 provides 720 compounds of formula IA wherein R1 is    hydrogen, R3 is dichloromethyl-, R4 is    3,5-bis(trifluoromethyl)phenyl-, Y1-Y2-Y3 is —N—CH2-CH2-, A2 is CH,    A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.    Table 137-   Table 137 provides 720 compounds of formula IA wherein R1 is    methyl-, R3 is dichloromethyl-, R4 is    3,5-bis(trifluoromethyl)phenyl-, Y1-Y2-Y3 is —N—CH2-CH2-, A2 is CH,    A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.    Table 138-   Table 138 provides 720 compounds of formula IA wherein R1 is ethyl-,    R3 is dichloromethyl-, R4 is 3,5-bis(trifluoromethyl)phenyl-,    Y1-Y2-Y3 is —N—CH2-CH2-, A2 is CH, A3 is CH, A4 is CH, and R5b, n    and R2 are as defined in Table P.    Table 139-   Table 139 provides 720 compounds of formula IA wherein R1 is    hydrogen, R3 is trifluoromethyl-, R4 is 3-(trifluoromethyl)phenyl-,    Y1-Y2-Y3 is —N—CH2-CH2-, A2 is CH, A3 is CH, A4 is CH, and R5b, n    and R2 are as defined in Table P.    Table 140-   Table 140 provides 720 compounds of formula IA wherein R1 is    methyl-, R3 is trifluoromethyl-, R4 is 3-(trifluoromethyl)phenyl-,    Y1-Y2-Y3 is —N—CH2-CH2-, A2 is CH, A3 is CH, A4 is CH, and R5b, n    and R2 are as defined in Table P.    Table 141-   Table 141 provides 720 compounds of formula IA wherein R1 is ethyl-,    R3 is trifluoromethyl-, R4 is 3-(trifluoromethyl)phenyl-, Y1-Y2-Y3    is —N—CH2-CH2-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are    as defined in Table P.    Table 142-   Table 142 provides 720 compounds of formula IA wherein R1 is    hydrogen, R3 is dichloromethyl-, R4 is 3-(trifluoromethyl)phenyl-,    Y1-Y2-Y3 is —N—CH2-CH2-, A2 is CH, A3 is CH, A4 is CH, and R5b, n    and R2 are as defined in Table P.    Table 143-   Table 143 provides 720 compounds of formula IA wherein R1 is    methyl-, R3 is dichloromethyl-, R4 is 3-(trifluoromethyl)phenyl-,    Y1-Y2-Y3 is —N—CH2-CH2-, A2 is CH, A3 is CH, A4 is CH, and R5b, n    and R2 are as defined in Table P.    Table 144-   Table 144 provides 720 compounds of formula IA wherein R1 is ethyl-,    R3 is dichloromethyl-, R4 is 3-(trifluoromethyl)phenyl-, Y1-Y2-Y3 is    —N—CH2-CH2-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 145-   Table 145 provides 720 compounds of formula IA wherein R1 is    hydrogen, R3 is trifluoromethyl-, R4 is 3,5-dichlorophenyl-,    Y1-Y2-Y3 is —C═CH—O—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and    R2 are as defined in Table P.    Table 146-   Table 146 provides 720 compounds of formula IA wherein R1 is    methyl-, R3 is trifluoromethyl-, R4 is 3,5-dichlorophenyl-, Y1-Y2-Y3    is —C═CH—O—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 147-   Table 147 provides 720 compounds of formula IA wherein R1 is ethyl-,    R3 is trifluoromethyl-, R4 is 3,5-dichlorophenyl-, Y1-Y2-Y3 is    —C═CH—O—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 148-   Table 148 provides 720 compounds of formula IA wherein R1 is    hydrogen, R3 is dichloromethyl-, R4 is 3,5-dichlorophenyl-, Y1-Y2-Y3    is —C═CH—O—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 149-   Table 149 provides 720 compounds of formula IA wherein R1 is    methyl-, R3 is dichloromethyl-, R4 is 3,5-dichlorophenyl-, Y1-Y2-Y3    is —C═CH—O—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 150-   Table 150 provides 720 compounds of formula IA wherein R1 is ethyl-,    R3 is dichloromethyl-, R4 is 3,5-dichlorophenyl-, Y1-Y2-Y3 is    —C═CH—O—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 151-   Table 151 provides 720 compounds of formula IA wherein R1 is    hydrogen, R3 is trifluoromethyl-, R4 is 3,4-dichlorophenyl-,    Y1-Y2-Y3 is —C═CH—O—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and    R2 are as defined in Table P.    Table 152-   Table 152 provides 720 compounds of formula IA wherein R1 is    methyl-, R3 is trifluoromethyl-, R4 is 3,4-dichlorophenyl-, Y1-Y2-Y3    is —C═CH—O—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 153-   Table 153 provides 720 compounds of formula IA wherein R1 is ethyl-,    R3 is trifluoromethyl-, R4 is 3,4-dichlorophenyl-, Y1-Y2-Y3 is    —C═CH—O—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 154-   Table 154 provides 720 compounds of formula IA wherein R1 is    hydrogen, R3 is dichloromethyl-, R4 is 3,4-dichlorophenyl-, Y1-Y2-Y3    is —C═CH—O—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 155-   Table 155 provides 720 compounds of formula IA wherein R1 is    methyl-, R3 is dichloromethyl-, R4 is 3,4-dichlorophenyl-, Y1-Y2-Y3    is —C═CH—O—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 156-   Table 156 provides 720 compounds of formula IA wherein R1 is ethyl-,    R3 is dichloromethyl-, R4 is 3,4-dichlorophenyl-, Y1-Y2-Y3 is    —C═CH—O—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 157-   Table 157 provides 720 compounds of formula IA wherein R1 is    hydrogen, R3 is trifluoromethyl-, R4 is    3,5-dichloro-4-fluorophenyl-, Y1-Y2-Y3 is —C═CH—O—, A2 is CH, A3 is    CH, A4 is CH, and R5b, n and R2 are as defined in Table P.    Table 158-   Table 158 provides 720 compounds of formula IA wherein R1 is    methyl-, R3 is trifluoromethyl-, R4 is 3,5-dichloro-4-fluorophenyl-,    Y1-Y2-Y3 is —C═CH—O—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and    R2 are as defined in Table P.    Table 159-   Table 159 provides 720 compounds of formula IA wherein R1 is ethyl-,    R3 is trifluoromethyl-, R4 is 3,5-dichloro-4-fluorophenyl-, Y1-Y2-Y3    is —C═CH—O—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 160-   Table 160 provides 720 compounds of formula IA wherein R1 is    hydrogen, R3 is dichloromethyl-, R4 is 3,5-dichloro-4-fluorophenyl-,    Y1-Y2-Y3 is —C═CH—O—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and    R2 are as defined in Table P.    Table 161-   Table 161 provides 720 compounds of formula IA wherein R1 is    methyl-, R3 is dichloromethyl-, R4 is 3,5-dichloro-4-fluorophenyl-,    Y1-Y2-Y3 is —C═CH—O—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and    R2 are as defined in Table P.    Table 162-   Table 162 provides 720 compounds of formula IA wherein R1 is ethyl-,    R3 is dichloromethyl-, R4 is 3,5-dichloro-4-fluorophenyl-, Y1-Y2-Y3    is —C═CH—O—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 163-   Table 163 provides 720 compounds of formula IA wherein R1 is    hydrogen, R3 is trifluoromethyl-, R4 is 3,4,5-trichlorophenyl-,    Y1-Y2-Y3 is —C═CH—O—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and    R2 are as defined in Table P.    Table 164-   Table 164 provides 720 compounds of formula IA wherein R1 is    methyl-, R3 is trifluoromethyl-, R4 is 3,4,5-trichlorophenyl-,    Y1-Y2-Y3 is —C═CH—O—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and    R2 are as defined in Table P.    Table 165-   Table 165 provides 720 compounds of formula IA wherein R1 is ethyl-,    R3 is trifluoromethyl-, R4 is 3,4,5-trichlorophenyl-, Y1-Y2-Y3 is    —C═CH—O—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 166-   Table 166 provides 720 compounds of formula IA wherein R1 is    hydrogen, R3 is dichloromethyl-, R4 is 3,4,5-trichlorophenyl-,    Y1-Y2-Y3 is —C═CH—O—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and    R2 are as defined in Table P.    Table 167-   Table 167 provides 720 compounds of formula IA wherein R1 is    methyl-, R3 is dichloromethyl-, R4 is 3,4,5-trichlorophenyl-,    Y1-Y2-Y3 is —C═CH—O—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and    R2 are as defined in Table P.    Table 168-   Table 168 provides 720 compounds of formula IA wherein R1 is ethyl-,    R3 is dichloromethyl-, R4 is 3,4,5-trichlorophenyl-, Y1-Y2-Y3 is    —C═CH—O—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 169-   Table 169 provides 720 compounds of formula IA wherein R1 is    hydrogen, R3 is trifluoromethyl-, R4 is 3-chloro-5-fluorophenyl-,    Y1-Y2-Y3 is —C═CH—O—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and    R2 are as defined in Table P.    Table 170-   Table 170 provides 720 compounds of formula IA wherein R1 is    methyl-, R3 is trifluoromethyl-, R4 is 3-chloro-5-fluorophenyl-,    Y1-Y2-Y3 is —C═CH—O—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and    R2 are as defined in Table P.    Table 171-   Table 171 provides 720 compounds of formula IA wherein R1 is ethyl-,    R3 is trifluoromethyl-, R4 is 3-chloro-5-fluorophenyl-, Y1-Y2-Y3 is    —C═CH—O—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 172-   Table 172 provides 720 compounds of formula IA wherein R1 is    hydrogen, R3 is dichloromethyl-, R4 is 3-chloro-5-fluorophenyl-,    Y1-Y2-Y3 is —C═CH—O—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and    R2 are as defined in Table P.    Table 173-   Table 173 provides 720 compounds of formula IA wherein R1 is    methyl-, R3 is dichloromethyl-, R4 is 3-chloro-5-fluorophenyl-,    Y1-Y2-Y3 is —C═CH—O—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and    R2 are as defined in Table P.    Table 174-   Table 174 provides 720 compounds of formula IA wherein R1 is ethyl-,    R3 is dichloromethyl-, R4 is 3-chloro-5-fluorophenyl-, Y1-Y2-Y3 is    —C═CH—O—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 175-   Table 175 provides 720 compounds of formula IA wherein R1 is    hydrogen, R3 is trifluoromethyl-, R4 is    3-chloro-5-(trifluoromethyl)phenyl-, Y1-Y2-Y3 is —C═CH—O—, A2 is CH,    A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.    Table 176-   Table 176 provides 720 compounds of formula IA wherein R1 is    methyl-, R3 is trifluoromethyl-, R4 is    3-chloro-5-(trifluoromethyl)phenyl-, Y1-Y2-Y3 is —C═CH—O—, A2 is CH,    A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.    Table 177-   Table 177 provides 720 compounds of formula IA wherein R1 is ethyl-,    R3 is trifluoromethyl-, R4 is 3-chloro-5-(trifluoromethyl)phenyl-,    Y1-Y2-Y3 is —C═CH—O—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and    R2 are as defined in Table P.    Table 178-   Table 178 provides 720 compounds of formula IA wherein R1 is    hydrogen, R3 is dichloromethyl-, R4 is    3-chloro-5-(trifluoromethyl)phenyl-, Y1-Y2-Y3 is —C═CH—O—, A2 is CH,    A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.    Table 179-   Table 179 provides 720 compounds of formula IA wherein R1 is    methyl-, R3 is dichloromethyl-, R4 is    3-chloro-5-(trifluoromethyl)phenyl-, Y1-Y2-Y3 is —C═CH—O—, A2 is CH,    A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.    Table 180-   Table 180 provides 720 compounds of formula IA wherein R1 is ethyl-,    R3 is dichloromethyl-, R4 is 3-chloro-5-(trifluoromethyl)phenyl-,    Y1-Y2-Y3 is —C═CH—O—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and    R2 are as defined in Table P.    Table 181-   Table 181 provides 720 compounds of formula IA wherein R1 is    hydrogen, R3 is trifluoromethyl-, R4 is    3,5-bis(trifluoromethyl)phenyl-, Y1-Y2-Y3 is —C═CH—O—, A2 is CH, A3    is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.    Table 182-   Table 182 provides 720 compounds of formula IA wherein R1 is    methyl-, R3 is trifluoromethyl-, R4 is    3,5-bis(trifluoromethyl)phenyl-, Y1-Y2-Y3 is —C═CH—O—, A2 is CH, A3    is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.    Table 183-   Table 183 provides 720 compounds of formula IA wherein R1 is ethyl-,    R3 is trifluoromethyl-, R4 is 3,5-bis(trifluoromethyl)phenyl-,    Y1-Y2-Y3 is —C═CH—O—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and    R2 are as defined in Table P.    Table 184-   Table 184 provides 720 compounds of formula IA wherein R1 is    hydrogen, R3 is dichloromethyl-, R4 is    3,5-bis(trifluoromethyl)phenyl-, Y1-Y2-Y3 is —C═CH—O—, A2 is CH, A3    is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.    Table 185-   Table 185 provides 720 compounds of formula IA wherein R1 is    methyl-, R3 is dichloromethyl-, R4 is    3,5-bis(trifluoromethyl)phenyl-, Y1-Y2-Y3 is —C═CH—O—, A2 is CH, A3    is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.    Table 186-   Table 186 provides 720 compounds of formula IA wherein R1 is ethyl-,    R3 is dichloromethyl-, R4 is 3,5-bis(trifluoromethyl)phenyl-,    Y1-Y2-Y3 is —C═CH—O—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and    R2 are as defined in Table P.    Table 187-   Table 187 provides 720 compounds of formula IA wherein R1 is    hydrogen, R3 is trifluoromethyl-, R4 is 3-(trifluoromethyl)phenyl-,    Y1-Y2-Y3 is —C═CH—O—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and    R2 are as defined in Table P.    Table 188-   Table 188 provides 720 compounds of formula IA wherein R1 is    methyl-, R3 is trifluoromethyl-, R4 is 3-(trifluoromethyl)phenyl-,    Y1-Y2-Y3 is —C═CH—O—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and    R2 are as defined in Table P.    Table 189-   Table 189 provides 720 compounds of formula IA wherein R1 is ethyl-,    R3 is trifluoromethyl-, R4 is 3-(trifluoromethyl)phenyl-, Y1-Y2-Y3    is —C═CH—O—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 190-   Table 190 provides 720 compounds of formula IA wherein R1 is    hydrogen, R3 is dichloromethyl-, R4 is 3-(trifluoromethyl)phenyl-,    Y1-Y2-Y3 is —C═CH—O—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and    R2 are as defined in Table P.    Table 191-   Table 191 provides 720 compounds of formula IA wherein R1 is    methyl-, R3 is dichloromethyl-, R4 is 3-(trifluoromethyl)phenyl-,    Y1-Y2-Y3 is —C═CH—O—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and    R2 are as defined in Table P.    Table 192-   Table 192 provides 720 compounds of formula IA wherein R1 is ethyl-,    R3 is dichloromethyl-, R4 is 3-(trifluoromethyl)phenyl-, Y1-Y2-Y3 is    —C═CH—O—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 193-   Table 193 provides 720 compounds of formula IA wherein R1 is    hydrogen, R3 is trifluoromethyl-, R4 is 3,5-dichlorophenyl-,    Y1-Y2-Y3 is —C═N—S—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2    are as defined in Table P.    Table 194-   Table 194 provides 720 compounds of formula IA wherein R1 is    methyl-, R3 is trifluoromethyl-, R4 is 3,5-dichlorophenyl-, Y1-Y2-Y3    is —C═N—S—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 195-   Table 195 provides 720 compounds of formula IA wherein R1 is ethyl-,    R3 is trifluoromethyl-, R4 is 3,5-dichlorophenyl-, Y1-Y2-Y3 is    —C═N—S—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 196-   Table 196 provides 720 compounds of formula IA wherein R1 is    hydrogen, R3 is dichloromethyl-, R4 is 3,5-dichlorophenyl-, Y1-Y2-Y3    is —C═N—S—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 197-   Table 197 provides 720 compounds of formula IA wherein R1 is    methyl-, R3 is dichloromethyl-, R4 is 3,5-dichlorophenyl-, Y1-Y2-Y3    is —C═N—S—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 198-   Table 198 provides 720 compounds of formula IA wherein R1 is ethyl-,    R3 is dichloromethyl-, R4 is 3,5-dichlorophenyl-, Y1-Y2-Y3 is    —C═N—S—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 199-   Table 199 provides 720 compounds of formula IA wherein R1 is    hydrogen, R3 is trifluoromethyl-, R4 is 3,4-dichlorophenyl-,    Y1-Y2-Y3 is —C═N—S—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2    are as defined in Table P.    Table 200-   Table 200 provides 720 compounds of formula IA wherein R1 is    methyl-, R3 is trifluoromethyl-, R4 is 3,4-dichlorophenyl-, Y1-Y2-Y3    is —C═N—S—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 201-   Table 201 provides 720 compounds of formula IA wherein R1 is ethyl-,    R3 is trifluoromethyl-, R4 is 3,4-dichlorophenyl-, Y1-Y2-Y3 is    —C═N—S—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 202-   Table 202 provides 720 compounds of formula IA wherein R1 is    hydrogen, R3 is dichloromethyl-, R4 is 3,4-dichlorophenyl-, Y1-Y2-Y3    is —C═N—S—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 203-   Table 203 provides 720 compounds of formula IA wherein R1 is    methyl-, R3 is dichloromethyl-, R4 is 3,4-dichlorophenyl-, Y1-Y2-Y3    is —C═N—S—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 204-   Table 204 provides 720 compounds of formula IA wherein R1 is ethyl-,    R3 is dichloromethyl-, R4 is 3,4-dichlorophenyl-, Y1-Y2-Y3 is    —C═N—S—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 205-   Table 205 provides 720 compounds of formula IA wherein R1 is    hydrogen, R3 is trifluoromethyl-, R4 is    3,5-dichloro-4-fluorophenyl-, Y1-Y2-Y3 is —C═N—S—, A2 is CH, A3 is    CH, A4 is CH, and R5b, n and R2 are as defined in Table P.    Table 206-   Table 206 provides 720 compounds of formula IA wherein R1 is    methyl-, R3 is trifluoromethyl-, R4 is 3,5-dichloro-4-fluorophenyl-,    Y1-Y2-Y3 is —C═N—S—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2    are as defined in Table P.    Table 207-   Table 207 provides 720 compounds of formula IA wherein R1 is ethyl-,    R3 is trifluoromethyl-, R4 is 3,5-dichloro-4-fluorophenyl-, Y1-Y2-Y3    is —C═N—S—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 208-   Table 208 provides 720 compounds of formula IA wherein R1 is    hydrogen, R3 is dichloromethyl-, R4 is 3,5-dichloro-4-fluorophenyl-,    Y1-Y2-Y3 is —C═N—S—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2    are as defined in Table P.    Table 209-   Table 209 provides 720 compounds of formula IA wherein R1 is    methyl-, R3 is dichloromethyl-, R4 is 3,5-dichloro-4-fluorophenyl-,    Y1-Y2-Y3 is —C═N—S—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2    are as defined in Table P.    Table 210-   Table 210 provides 720 compounds of formula IA wherein R1 is ethyl-,    R3 is dichloromethyl-, R4 is 3,5-dichloro-4-fluorophenyl-, Y1-Y2-Y3    is —C═N—S—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 211-   Table 211 provides 720 compounds of formula IA wherein R1 is    hydrogen, R3 is trifluoromethyl-, R4 is 3,4,5-trichlorophenyl-,    Y1-Y2-Y3 is —C═N—S—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2    are as defined in Table P.    Table 212-   Table 212 provides 720 compounds of formula IA wherein R1 is    methyl-, R3 is trifluoromethyl-, R4 is 3,4,5-trichlorophenyl-,    Y1-Y2-Y3 is —C═N—S—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2    are as defined in Table P.    Table 213-   Table 213 provides 720 compounds of formula IA wherein R1 is ethyl-,    R3 is trifluoromethyl-, R4 is 3,4,5-trichlorophenyl-, Y1-Y2-Y3 is    —C═N—S—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 214-   Table 214 provides 720 compounds of formula IA wherein R1 is    hydrogen, R3 is dichloromethyl-, R4 is 3,4,5-trichlorophenyl-,    Y1-Y2-Y3 is —C═N—S—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2    are as defined in Table P.    Table 215-   Table 215 provides 720 compounds of formula IA wherein R1 is    methyl-, R3 is dichloromethyl-, R4 is 3,4,5-trichlorophenyl-,    Y1-Y2-Y3 is —C═N—S—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2    are as defined in Table P.    Table 216-   Table 216 provides 720 compounds of formula IA wherein R1 is ethyl-,    R3 is dichloromethyl-, R4 is 3,4,5-trichlorophenyl-, Y1-Y2-Y3 is    —C═N—S—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 217-   Table 217 provides 720 compounds of formula IA wherein R1 is    hydrogen, R3 is trifluoromethyl-, R4 is 3-chloro-5-fluorophenyl-,    Y1-Y2-Y3 is —C═N—S—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2    are as defined in Table P.    Table 218-   Table 218 provides 720 compounds of formula IA wherein R1 is    methyl-, R3 is trifluoromethyl-, R4 is 3-chloro-5-fluorophenyl-,    Y1-Y2-Y3 is —C═N—S—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2    are as defined in Table P.    Table 219-   Table 219 provides 720 compounds of formula IA wherein R1 is ethyl-,    R3 is trifluoromethyl-, R4 is 3-chloro-5-fluorophenyl-, Y1-Y2-Y3 is    —C═N—S—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 220-   Table 220 provides 720 compounds of formula IA wherein R1 is    hydrogen, R3 is dichloromethyl-, R4 is 3-chloro-5-fluorophenyl-,    Y1-Y2-Y3 is —C═N—S—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2    are as defined in Table P.    Table 221-   Table 221 provides 720 compounds of formula IA wherein R1 is    methyl-, R3 is dichloromethyl-, R4 is 3-chloro-5-fluorophenyl-,    Y1-Y2-Y3 is —C═N—S—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2    are as defined in Table P.    Table 222-   Table 222 provides 720 compounds of formula IA wherein R1 is ethyl-,    R3 is dichloromethyl-, R4 is 3-chloro-5-fluorophenyl-, Y1-Y2-Y3 is    —C═N—S—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 223-   Table 223 provides 720 compounds of formula IA wherein R1 is    hydrogen, R3 is trifluoromethyl-, R4 is    3-chloro-5-(trifluoromethyl)phenyl-, Y1-Y2-Y3 is —C═N—S—, A2 is CH,    A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.    Table 224-   Table 224 provides 720 compounds of formula IA wherein R1 is    methyl-, R3 is trifluoromethyl-, R4 is    3-chloro-5-(trifluoromethyl)phenyl-, Y1-Y2-Y3 is —C═N—S—, A2 is CH,    A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.    Table 225-   Table 225 provides 720 compounds of formula IA wherein R1 is ethyl-,    R3 is trifluoromethyl-, R4 is 3-chloro-5-(trifluoromethyl)phenyl-,    Y1-Y2-Y3 is —C═N—S—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2    are as defined in Table P.    Table 226-   Table 226 provides 720 compounds of formula IA wherein R1 is    hydrogen, R3 is dichloromethyl-, R4 is    3-chloro-5-(trifluoromethyl)phenyl-, Y1-Y2-Y3 is —C═N—S—, A2 is CH,    A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.    Table 227-   Table 227 provides 720 compounds of formula IA wherein R1 is    methyl-, R3 is dichloromethyl-, R4 is    3-chloro-5-(trifluoromethyl)phenyl-, Y1-Y2-Y3 is —C═N—S—, A2 is CH,    A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.    Table 228-   Table 228 provides 720 compounds of formula IA wherein R1 is ethyl-,    R3 is dichloromethyl-, R4 is 3-chloro-5-(trifluoromethyl)phenyl-,    Y1-Y2-Y3 is —C═N—S—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2    are as defined in Table P.    Table 229-   Table 229 provides 720 compounds of formula IA wherein R1 is    hydrogen, R3 is trifluoromethyl-, R4 is    3,5-bis(trifluoromethyl)phenyl-, Y1-Y2-Y3 is —C═N—S—, A2 is CH, A3    is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.    Table 230-   Table 230 provides 720 compounds of formula IA wherein R1 is    methyl-, R3 is trifluoromethyl-, R4 is    3,5-bis(trifluoromethyl)phenyl-, Y1-Y2-Y3 is —C═N—S—, A2 is CH, A3    is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.    Table 231-   Table 231 provides 720 compounds of formula IA wherein R1 is ethyl-,    R3 is trifluoromethyl-, R4 is 3,5-bis(trifluoromethyl)phenyl-,    Y1-Y2-Y3 is —C═N—S—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2    are as defined in Table P.    Table 232-   Table 232 provides 720 compounds of formula IA wherein R1 is    hydrogen, R3 is dichloromethyl-, R4 is    3,5-bis(trifluoromethyl)phenyl-, Y1-Y2-Y3 is —C═N—S—, A2 is CH, A3    is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.    Table 233-   Table 233 provides 720 compounds of formula IA wherein R1 is    methyl-, R3 is dichloromethyl-, R4 is    3,5-bis(trifluoromethyl)phenyl-, Y1-Y2-Y3 is —C═N—S—, A2 is CH, A3    is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.    Table 234-   Table 234 provides 720 compounds of formula IA wherein R1 is ethyl-,    R3 is dichloromethyl-, R4 is 3,5-bis(trifluoromethyl)phenyl-,    Y1-Y2-Y3 is —C═N—S—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2    are as defined in Table P.    Table 235-   Table 235 provides 720 compounds of formula IA wherein R1 is    hydrogen, R3 is trifluoromethyl-, R4 is 3-(trifluoromethyl)phenyl-,    Y1-Y2-Y3 is —C═N—S—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2    are as defined in Table P.    Table 236-   Table 236 provides 720 compounds of formula IA wherein R1 is    methyl-, R3 is trifluoromethyl-, R4 is 3-(trifluoromethyl)phenyl-,    Y1-Y2-Y3 is —C═N—S—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2    are as defined in Table P.    Table 237-   Table 237 provides 720 compounds of formula IA wherein R1 is ethyl-,    R3 is trifluoromethyl-, R4 is 3-(trifluoromethyl)phenyl-, Y1-Y2-Y3    is —C═N—S—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 238-   Table 238 provides 720 compounds of formula IA wherein R1 is    hydrogen, R3 is dichloromethyl-, R4 is 3-(trifluoromethyl)phenyl-,    Y1-Y2-Y3 is —C═N—S—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2    are as defined in Table P.    Table 239-   Table 239 provides 720 compounds of formula IA wherein R1 is    methyl-, R3 is dichloromethyl-, R4 is 3-(trifluoromethyl)phenyl-,    Y1-Y2-Y3 is —C═N—S—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2    are as defined in Table P.    Table 240-   Table 240 provides 720 compounds of formula IA wherein R1 is ethyl-,    R3 is dichloromethyl-, R4 is 3-(trifluoromethyl)phenyl-, Y1-Y2-Y3 is    —C═N—S—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 241-   Table 241 provides 720 compounds of formula IA wherein R1 is    hydrogen, R3 is trifluoromethyl-, R4 is 3,5-dichlorophenyl-,    Y1-Y2-Y3 is —C═CH—S—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and    R2 are as defined in Table P.    Table 242-   Table 242 provides 720 compounds of formula IA wherein R1 is    methyl-, R3 is trifluoromethyl-, R4 is 3,5-dichlorophenyl-, Y1-Y2-Y3    is —C═CH—S—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 243-   Table 243 provides 720 compounds of formula IA wherein R1 is ethyl-,    R3 is trifluoromethyl-, R4 is 3,5-dichlorophenyl-, Y1-Y2-Y3 is    —C═CH—S—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 244-   Table 244 provides 720 compounds of formula IA wherein R1 is    hydrogen, R3 is dichloromethyl-, R4 is 3,5-dichlorophenyl-, Y1-Y2-Y3    is —C═CH—S—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 245-   Table 245 provides 720 compounds of formula IA wherein R1 is    methyl-, R3 is dichloromethyl-, R4 is 3,5-dichlorophenyl-, Y1-Y2-Y3    is —C═CH—S—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 246-   Table 246 provides 720 compounds of formula IA wherein R1 is ethyl-,    R3 is dichloromethyl-, R4 is 3,5-dichlorophenyl-, Y1-Y2-Y3 is    —C═CH—S—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 247-   Table 247 provides 720 compounds of formula IA wherein R1 is    hydrogen, R3 is trifluoromethyl-, R4 is 3,4-dichlorophenyl-,    Y1-Y2-Y3 is —C═CH—S—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and    R2 are as defined in Table P.    Table 248-   Table 248 provides 720 compounds of formula IA wherein R1 is    methyl-, R3 is trifluoromethyl-, R4 is 3,4-dichlorophenyl-, Y1-Y2-Y3    is —C═CH—S—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 249-   Table 249 provides 720 compounds of formula IA wherein R1 is ethyl-,    R3 is trifluoromethyl-, R4 is 3,4-dichlorophenyl-, Y1-Y2-Y3 is    —C═CH—S—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 250-   Table 250 provides 720 compounds of formula IA wherein R1 is    hydrogen, R3 is dichloromethyl-, R4 is 3,4-dichlorophenyl-, Y1-Y2-Y3    is —C═CH—S—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 251-   Table 251 provides 720 compounds of formula IA wherein R1 is    methyl-, R3 is dichloromethyl-, R4 is 3,4-dichlorophenyl-, Y1-Y2-Y3    is —C═CH—S—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 252-   Table 252 provides 720 compounds of formula IA wherein R1 is ethyl-,    R3 is dichloromethyl-, R4 is 3,4-dichlorophenyl-, Y1-Y2-Y3 is    —C═CH—S—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 253-   Table 253 provides 720 compounds of formula IA wherein R1 is    hydrogen, R3 is trifluoromethyl-, R4 is    3,5-dichloro-4-fluorophenyl-, Y1-Y2-Y3 is —C═CH—S—, A2 is CH, A3 is    CH, A4 is CH, and R5b, n and R2 are as defined in Table P.    Table 254-   Table 254 provides 720 compounds of formula IA wherein R1 is    methyl-, R3 is trifluoromethyl-, R4 is 3,5-dichloro-4-fluorophenyl-,    Y1-Y2-Y3 is —C═CH—S—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and    R2 are as defined in Table P.    Table 255-   Table 255 provides 720 compounds of formula IA wherein R1 is ethyl-,    R3 is trifluoromethyl-, R4 is 3,5-dichloro-4-fluorophenyl-, Y1-Y2-Y3    is —C═CH—S—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 256-   Table 256 provides 720 compounds of formula IA wherein R1 is    hydrogen, R3 is dichloromethyl-, R4 is 3,5-dichloro-4-fluorophenyl-,    Y1-Y2-Y3 is —C═CH—S—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and    R2 are as defined in Table P.    Table 257-   Table 257 provides 720 compounds of formula IA wherein R1 is    methyl-, R3 is dichloromethyl-, R4 is 3,5-dichloro-4-fluorophenyl-,    Y1-Y2-Y3 is —C═CH—S—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and    R2 are as defined in Table P.    Table 258-   Table 258 provides 720 compounds of formula IA wherein R1 is ethyl-,    R3 is dichloromethyl-, R4 is 3,5-dichloro-4-fluorophenyl-, Y1-Y2-Y3    is —C═CH—S—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 259-   Table 259 provides 720 compounds of formula IA wherein R1 is    hydrogen, R3 is trifluoromethyl-, R4 is 3,4,5-trichlorophenyl-,    Y1-Y2-Y3 is —C═CH—S—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and    R2 are as defined in Table P.    Table 260-   Table 260 provides 720 compounds of formula IA wherein R1 is    methyl-, R3 is trifluoromethyl-, R4 is 3,4,5-trichlorophenyl-,    Y1-Y2-Y3 is —C═CH—S—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and    R2 are as defined in Table P.    Table 261-   Table 261 provides 720 compounds of formula IA wherein R1 is ethyl-,    R3 is trifluoromethyl-, R4 is 3,4,5-trichlorophenyl-, Y1-Y2-Y3 is    —C═CH—S—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 262-   Table 262 provides 720 compounds of formula IA wherein R1 is    hydrogen, R3 is dichloromethyl-, R4 is 3,4,5-trichlorophenyl-,    Y1-Y2-Y3 is —C═CH—S—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and    R2 are as defined in Table P.    Table 263-   Table 263 provides 720 compounds of formula IA wherein R1 is    methyl-, R3 is dichloromethyl-, R4 is 3,4,5-trichlorophenyl-,    Y1-Y2-Y3 is —C═CH—S—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and    R2 are as defined in Table P.    Table 264-   Table 264 provides 720 compounds of formula IA wherein R1 is ethyl-,    R3 is dichloromethyl-, R4 is 3,4,5-trichlorophenyl-, Y1-Y2-Y3 is    —C═CH—S—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 265-   Table 265 provides 720 compounds of formula IA wherein R1 is    hydrogen, R3 is trifluoromethyl-, R4 is 3-chloro-5-fluorophenyl-,    Y1-Y2-Y3 is —C═CH—S—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and    R2 are as defined in Table P.    Table 266-   Table 266 provides 720 compounds of formula IA wherein R1 is    methyl-, R3 is trifluoromethyl-, R4 is 3-chloro-5-fluorophenyl-,    Y1-Y2-Y3 is —C═CH—S—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and    R2 are as defined in Table P.    Table 267-   Table 267 provides 720 compounds of formula IA wherein R1 is ethyl-,    R3 is trifluoromethyl-, R4 is 3-chloro-5-fluorophenyl-, Y1-Y2-Y3 is    —C═CH—S—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 268-   Table 268 provides 720 compounds of formula IA wherein R1 is    hydrogen, R3 is dichloromethyl-, R4 is 3-chloro-5-fluorophenyl-,    Y1-Y2-Y3 is —C═CH—S—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and    R2 are as defined in Table P.    Table 269-   Table 269 provides 720 compounds of formula IA wherein R1 is    methyl-, R3 is dichloromethyl-, R4 is 3-chloro-5-fluorophenyl-,    Y1-Y2-Y3 is —C═CH—S—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and    R2 are as defined in Table P.    Table 270-   Table 270 provides 720 compounds of formula IA wherein R1 is ethyl-,    R3 is dichloromethyl-, R4 is 3-chloro-5-fluorophenyl-, Y1-Y2-Y3 is    —C═CH—S—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 271-   Table 271 provides 720 compounds of formula IA wherein R1 is    hydrogen, R3 is trifluoromethyl-, R4 is    3-chloro-5-(trifluoromethyl)phenyl-, Y1-Y2-Y3 is —C═CH—S—, A2 is CH,    A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.    Table 272-   Table 272 provides 720 compounds of formula IA wherein R1 is    methyl-, R3 is trifluoromethyl-, R4 is    3-chloro-5-(trifluoromethyl)phenyl-, Y1-Y2-Y3 is —C═CH—S—, A2 is CH,    A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.    Table 273-   Table 273 provides 720 compounds of formula IA wherein R1 is ethyl-,    R3 is trifluoromethyl-, R4 is 3-chloro-5-(trifluoromethyl)phenyl-,    Y1-Y2-Y3 is —C═CH—S—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and    R2 are as defined in Table P.    Table 274-   Table 274 provides 720 compounds of formula IA wherein R1 is    hydrogen, R3 is dichloromethyl-, R4 is    3-chloro-5-(trifluoromethyl)phenyl-, Y1-Y2-Y3 is —C═CH—S—, A2 is CH,    A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.    Table 275-   Table 275 provides 720 compounds of formula IA wherein R1 is    methyl-, R3 is dichloromethyl-, R4 is    3-chloro-5-(trifluoromethyl)phenyl-, Y1-Y2-Y3 is —C═CH—S—, A2 is CH,    A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.    Table 276-   Table 276 provides 720 compounds of formula IA wherein R1 is ethyl-,    R3 is dichloromethyl-, R4 is 3-chloro-5-(trifluoromethyl)phenyl-,    Y1-Y2-Y3 is —C═CH—S—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and    R2 are as defined in Table P.    Table 277-   Table 277 provides 720 compounds of formula IA wherein R1 is    hydrogen, R3 is trifluoromethyl-, R4 is    3,5-bis(trifluoromethyl)phenyl-, Y1-Y2-Y3 is —C═CH—S—, A2 is CH, A3    is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.    Table 278-   Table 278 provides 720 compounds of formula IA wherein R1 is    methyl-, R3 is trifluoromethyl-, R4 is    3,5-bis(trifluoromethyl)phenyl-, Y1-Y2-Y3 is —C═CH—S—, A2 is CH, A3    is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.    Table 279-   Table 279 provides 720 compounds of formula IA wherein R1 is ethyl-,    R3 is trifluoromethyl-, R4 is 3,5-bis(trifluoromethyl)phenyl-,    Y1-Y2-Y3 is —C═CH—S—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and    R2 are as defined in Table P.    Table 280-   Table 280 provides 720 compounds of formula IA wherein R1 is    hydrogen, R3 is dichloromethyl-, R4 is    3,5-bis(trifluoromethyl)phenyl-, Y1-Y2-Y3 is —C═CH—S—, A2 is CH, A3    is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.    Table 281-   Table 281 provides 720 compounds of formula IA wherein R1 is    methyl-, R3 is dichloromethyl-, R4 is    3,5-bis(trifluoromethyl)phenyl-, Y1-Y2-Y3 is —C═CH—S—, A2 is CH, A3    is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.    Table 282-   Table 282 provides 720 compounds of formula IA wherein R1 is ethyl-,    R3 is dichloromethyl-, R4 is 3,5-bis(trifluoromethyl)phenyl-,    Y1-Y2-Y3 is —C═CH—S—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and    R2 are as defined in Table P.    Table 283-   Table 283 provides 720 compounds of formula IA wherein R1 is    hydrogen, R3 is trifluoromethyl-, R4 is 3-(trifluoromethyl)phenyl-,    Y1-Y2-Y3 is —C═CH—S—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and    R2 are as defined in Table P.    Table 284-   Table 284 provides 720 compounds of formula IA wherein R1 is    methyl-, R3 is trifluoromethyl-, R4 is 3-(trifluoromethyl)phenyl-,    Y1-Y2-Y3 is —C═CH—S—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and    R2 are as defined in Table P.    Table 285-   Table 285 provides 720 compounds of formula IA wherein R1 is ethyl-,    R3 is trifluoromethyl-, R4 is 3-(trifluoromethyl)phenyl-, Y1-Y2-Y3    is —C═CH—S—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.    Table 286-   Table 286 provides 720 compounds of formula IA wherein R1 is    hydrogen, R3 is dichloromethyl-, R4 is 3-(trifluoromethyl)phenyl-,    Y1-Y2-Y3 is —C═CH—S—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and    R2 are as defined in Table P.    Table 287-   Table 287 provides 720 compounds of formula IA wherein R1 is    methyl-, R3 is dichloromethyl-, R4 is 3-(trifluoromethyl)phenyl-,    Y1-Y2-Y3 is —C═CH—S—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and    R2 are as defined in Table P.    Table 288-   Table 288 provides 720 compounds of formula IA wherein R1 is ethyl-,    R3 is dichloromethyl-, R4 is 3-(trifluoromethyl)phenyl-, Y1-Y2-Y3 is    —C═CH—S—, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as    defined in Table P.

TABLE Q R5b n R3 R4 1 methyl- 0 trifluoromethyl- 3,5-dichlorophenyl- 2chloro- 0 trifluoromethyl- 3,5-dichlorophenyl- 3 bromo- 0trifluoromethyl- 3,5-dichlorophenyl- 4 trifluoromethyl- 0trifluoromethyl- 3,5-dichlorophenyl- 5 methyl- 1 trifluoromethyl-3,5-dichlorophenyl- 6 chloro- 1 trifluoromethyl- 3,5-dichlorophenyl- 7bromo- 1 trifluoromethyl- 3,5-dichlorophenyl- 8 trifluoromethyl- 1trifluoromethyl- 3,5-dichlorophenyl- 9 methyl- 2 trifluoromethyl-3,5-dichlorophenyl- 10 chloro- 2 trifluoromethyl- 3,5-dichlorophenyl- 11bromo- 2 trifluoromethyl- 3,5-dichlorophenyl- 12 trifluoromethyl- 2trifluoromethyl- 3,5-dichlorophenyl- 13 methyl- 0 dichloromethyl-3,5-dichlorophenyl- 14 chloro- 0 dichloromethyl- 3,5-dichlorophenyl- 15bromo- 0 dichloromethyl- 3,5-dichlorophenyl- 16 trifluoromethyl- 0dichloromethyl- 3,5-dichlorophenyl- 17 methyl- 1 dichloromethyl-3,5-dichlorophenyl- 18 chloro- 1 dichloromethyl- 3,5-dichlorophenyl- 19bromo- 1 dichloromethyl- 3,5-dichlorophenyl- 20 trifluoromethyl- 1dichloromethyl- 3,5-dichlorophenyl- 21 methyl- 2 dichloromethyl-3,5-dichlorophenyl- 22 chloro- 2 dichloromethyl- 3,5-dichlorophenyl- 23bromo- 2 dichloromethyl- 3,5-dichlorophenyl- 24 trifluoromethyl- 2dichloromethyl- 3,5-dichlorophenyl- 25 methyl- 0 trifluoromethyl-3,4-dichlorophenyl- 26 chloro- 0 trifluoromethyl- 3,4-dichlorophenyl- 27bromo- 0 trifluoromethyl- 3,4-dichlorophenyl- 28 trifluoromethyl- 0trifluoromethyl- 3,4-dichlorophenyl- 29 methyl- 1 trifluoromethyl-3,4-dichlorophenyl- 30 chloro- 1 trifluoromethyl- 3,4-dichlorophenyl- 31bromo- 1 trifluoromethyl- 3,4-dichlorophenyl- 32 trifluoromethyl- 1trifluoromethyl- 3,4-dichlorophenyl- 33 methyl- 2 trifluoromethyl-3,4-dichlorophenyl- 34 chloro- 2 trifluoromethyl- 3,4-dichlorophenyl- 35bromo- 2 trifluoromethyl- 3,4-dichlorophenyl- 36 trifluoromethyl- 2trifluoromethyl- 3,4-dichlorophenyl- 37 methyl- 0 dichloromethyl-3,4-dichlorophenyl- 38 chloro- 0 dichloromethyl- 3,4-dichlorophenyl- 39bromo- 0 dichloromethyl- 3,4-dichlorophenyl- 40 trifluoromethyl- 0dichloromethyl- 3,4-dichlorophenyl- 41 methyl- 1 dichloromethyl-3,4-dichlorophenyl- 42 chloro- 1 dichloromethyl- 3,4-dichlorophenyl- 43bromo- 1 dichloromethyl- 3,4-dichlorophenyl- 44 trifluoromethyl- 1dichloromethyl- 3,4-dichlorophenyl- 45 methyl- 2 dichloromethyl-3,4-dichlorophenyl- 46 chloro- 2 dichloromethyl- 3,4-dichlorophenyl- 47bromo- 2 dichloromethyl- 3,4-dichlorophenyl- 48 trifluoromethyl- 2dichloromethyl- 3,4-dichlorophenyl- 49 methyl- 0 trifluoromethyl-3,5-dichloro-4-fluorophenyl- 50 chloro- 0 trifluoromethyl-3,5-dichloro-4-fluorophenyl- 51 bromo- 0 trifluoromethyl-3,5-dichloro-4-fluorophenyl- 52 trifluoromethyl- 0 trifluoromethyl-3,5-dichloro-4-fluorophenyl- 53 methyl- 1 trifluoromethyl-3,5-dichloro-4-fluorophenyl- 54 chloro- 1 trifluoromethyl-3,5-dichloro-4-fluorophenyl- 55 bromo- 1 trifluoromethyl-3,5-dichloro-4-fluorophenyl- 56 trifluoromethyl- 1 trifluoromethyl-3,5-dichloro-4-fluorophenyl- 57 methyl- 2 trifluoromethyl-3,5-dichloro-4-fluorophenyl- 58 chloro- 2 trifluoromethyl-3,5-dichloro-4-fluorophenyl- 59 bromo- 2 trifluoromethyl-3,5-dichloro-4-fluorophenyl- 60 trifluoromethyl- 2 trifluoromethyl-3,5-dichloro-4-fluorophenyl- 61 methyl- 0 dichloromethyl-3,5-dichloro-4-fluorophenyl- 62 chloro- 0 dichloromethyl-3,5-dichloro-4-fluorophenyl- 63 bromo- 0 dichloromethyl-3,5-dichloro-4-fluorophenyl- 64 trifluoromethyl- 0 dichloromethyl-3,5-dichloro-4-fluorophenyl- 65 methyl- 1 dichloromethyl-3,5-dichloro-4-fluorophenyl- 66 chloro- 1 dichloromethyl-3,5-dichloro-4-fluorophenyl- 67 bromo- 1 dichloromethyl-3,5-dichloro-4-fluorophenyl- 68 trifluoromethyl- 1 dichloromethyl-3,5-dichloro-4-fluorophenyl- 69 methyl- 2 dichloromethyl-3,5-dichloro-4-fluorophenyl- 70 chloro- 2 dichloromethyl-3,5-dichloro-4-fluorophenyl- 71 bromo- 2 dichloromethyl-3,5-dichloro-4-fluorophenyl- 72 trifluoromethyl- 2 dichloromethyl-3,5-dichloro-4-fluorophenyl- 73 methyl- 0 trifluoromethyl-3,4,5-trichlorophenyl- 74 chloro- 0 trifluoromethyl-3,4,5-trichlorophenyl- 75 bromo- 0 trifluoromethyl-3,4,5-trichlorophenyl- 76 trifluoromethyl- 0 trifluoromethyl-3,4,5-trichlorophenyl- 77 methyl- 1 trifluoromethyl-3,4,5-trichlorophenyl- 78 chloro- 1 trifluoromethyl-3,4,5-trichlorophenyl- 79 bromo- 1 trifluoromethyl-3,4,5-trichlorophenyl- 80 trifluoromethyl- 1 trifluoromethyl-3,4,5-trichlorophenyl- 81 methyl- 2 trifluoromethyl-3,4,5-trichlorophenyl- 82 chloro- 2 trifluoromethyl-3,4,5-trichlorophenyl- 83 bromo- 2 trifluoromethyl-3,4,5-trichlorophenyl- 84 trifluoromethyl- 2 trifluoromethyl-3,4,5-trichlorophenyl- 85 methyl- 0 dichloromethyl-3,4,5-trichlorophenyl- 86 chloro- 0 dichloromethyl-3,4,5-trichlorophenyl- 87 bromo- 0 dichloromethyl-3,4,5-trichlorophenyl- 88 trifluoromethyl- 0 dichloromethyl-3,4,5-trichlorophenyl- 89 methyl- 1 dichloromethyl-3,4,5-trichlorophenyl- 90 chloro- 1 dichloromethyl-3,4,5-trichlorophenyl- 91 bromo- 1 dichloromethyl-3,4,5-trichlorophenyl- 92 trifluoromethyl- 1 dichloromethyl-3,4,5-trichlorophenyl- 93 methyl- 2 dichloromethyl-3,4,5-trichlorophenyl- 94 chloro- 2 dichloromethyl-3,4,5-trichlorophenyl- 95 bromo- 2 dichloromethyl-3,4,5-trichlorophenyl- 96 trifluoromethyl- 2 dichloromethyl-3,4,5-trichlorophenyl- 97 methyl- 0 trifluoromethyl-3-chloro-5-fluorophenyl- 98 chloro- 0 trifluoromethyl-3-chloro-5-fluorophenyl- 99 bromo- 0 trifluoromethyl-3-chloro-5-fluorophenyl- 100 trifluoromethyl- 0 trifluoromethyl-3-chloro-5-fluorophenyl- 101 methyl- 1 trifluoromethyl-3-chloro-5-fluorophenyl- 102 chloro- 1 trifluoromethyl-3-chloro-5-fluorophenyl- 103 bromo- 1 trifluoromethyl-3-chloro-5-fluorophenyl- 104 trifluoromethyl- 1 trifluoromethyl-3-chloro-5-fluorophenyl- 105 methyl- 2 trifluoromethyl-3-chloro-5-fluorophenyl- 106 chloro- 2 trifluoromethyl-3-chloro-5-fluorophenyl- 107 bromo- 2 trifluoromethyl-3-chloro-5-fluorophenyl- 108 trifluoromethyl- 2 trifluoromethyl-3-chloro-5-fluorophenyl- 109 methyl- 0 dichloromethyl-3-chloro-5-fluorophenyl- 110 chloro- 0 dichloromethyl-3-chloro-5-fluorophenyl- 111 bromo- 0 dichloromethyl-3-chloro-5-fluorophenyl- 112 trifluoromethyl- 0 dichloromethyl-3-chloro-5-fluorophenyl- 113 methyl- 1 dichloromethyl-3-chloro-5-fluorophenyl- 114 chloro- 1 dichloromethyl-3-chloro-5-fluorophenyl- 115 bromo- 1 dichloromethyl-3-chloro-5-fluorophenyl- 116 trifluoromethyl- 1 dichloromethyl-3-chloro-5-fluorophenyl- 117 methyl- 2 dichloromethyl-3-chloro-5-fluorophenyl- 118 chloro- 2 dichloromethyl-3-chloro-5-fluorophenyl- 119 bromo- 2 dichloromethyl-3-chloro-5-fluorophenyl- 120 trifluoromethyl- 2 dichloromethyl-3-chloro-5-fluorophenyl- 121 methyl- 0 trifluoromethyl-3-chloro-5-(trifluoromethyl)phenyl- 122 chloro- 0 trifluoromethyl-3-chloro-5-(trifluoromethyl)phenyl- 123 bromo- 0 trifluoromethyl-3-chloro-5-(trifluoromethyl)phenyl- 124 trifluoromethyl- 0trifluoromethyl- 3-chloro-5-(trifluoromethyl)phenyl- 125 methyl- 1trifluoromethyl- 3-chloro-5-(trifluoromethyl)phenyl- 126 chloro- 1trifluoromethyl- 3-chloro-5-(trifluoromethyl)phenyl- 127 bromo- 1trifluoromethyl- 3-chloro-5-(trifluoromethyl)phenyl- 128trifluoromethyl- 1 trifluoromethyl- 3-chloro-5-(trifluoromethyl)phenyl-129 methyl- 2 trifluoromethyl- 3-chloro-5-(trifluoromethyl)phenyl- 130chloro- 2 trifluoromethyl- 3-chloro-5-(trifluoromethyl)phenyl- 131bromo- 2 trifluoromethyl- 3-chloro-5-(trifluoromethyl)phenyl- 132trifluoromethyl- 2 trifluoromethyl- 3-chloro-5-(trifluoromethyl)phenyl-133 methyl- 0 dichloromethyl- 3-chloro-5-(trifluoromethyl)phenyl- 134chloro- 0 dichloromethyl- 3-chloro-5-(trifluoromethyl)phenyl- 135 bromo-0 dichloromethyl- 3-chloro-5-(trifluoromethyl)phenyl- 136trifluoromethyl- 0 dichloromethyl- 3-chloro-5-(trifluoromethyl)phenyl-137 methyl- 1 dichloromethyl- 3-chloro-5-(trifluoromethyl)phenyl- 138chloro- 1 dichloromethyl- 3-chloro-5-(trifluoromethyl)phenyl- 139 bromo-1 dichloromethyl- 3-chloro-5-(trifluoromethyl)phenyl- 140trifluoromethyl- 1 dichloromethyl- 3-chloro-5-(trifluoromethyl)phenyl-141 methyl- 2 dichloromethyl- 3-chloro-5-(trifluoromethyl)phenyl- 142chloro- 2 dichloromethyl- 3-chloro-5-(trifluoromethyl)phenyl- 143 bromo-2 dichloromethyl- 3-chloro-5-(trifluoromethyl)phenyl- 144trifluoromethyl- 2 dichloromethyl- 3-chloro-5-(trifluoromethyl)phenyl-145 methyl- 0 trifluoromethyl- 3,5-bis(trifluoromethyl)phenyl- 146chloro- 0 trifluoromethyl- 3,5-bis(trifluoromethyl)phenyl- 147 bromo- 0trifluoromethyl- 3,5-bis(trifluoromethyl)phenyl- 148 trifluoromethyl- 0trifluoromethyl- 3,5-bis(trifluoromethyl)phenyl- 149 methyl- 1trifluoromethyl- 3,5-bis(trifluoromethyl)phenyl- 150 chloro- 1trifluoromethyl- 3,5-bis(trifluoromethyl)phenyl- 151 bromo- 1trifluoromethyl- 3,5-bis(trifluoromethyl)phenyl- 152 trifluoromethyl- 1trifluoromethyl- 3,5-bis(trifluoromethyl)phenyl- 153 methyl- 2trifluoromethyl- 3,5-bis(trifluoromethyl)phenyl- 154 chloro- 2trifluoromethyl- 3,5-bis(trifluoromethyl)phenyl- 155 bromo- 2trifluoromethyl- 3,5-bis(trifluoromethyl)phenyl- 156 trifluoromethyl- 2trifluoromethyl- 3,5-bis(trifluoromethyl)phenyl- 157 methyl- 0dichloromethyl- 3,5-bis(trifluoromethyl)phenyl- 158 chloro- 0dichloromethyl- 3,5-bis(trifluoromethyl)phenyl- 159 bromo- 0dichloromethyl- 3,5-bis(trifluoromethyl)phenyl- 160 trifluoromethyl- 0dichloromethyl- 3,5-bis(trifluoromethyl)phenyl- 161 methyl- 1dichloromethyl- 3,5-bis(trifluoromethyl)phenyl- 162 chloro- 1dichloromethyl- 3,5-bis(trifluoromethyl)phenyl- 163 bromo- 1dichloromethyl- 3,5-bis(trifluoromethyl)phenyl- 164 trifluoromethyl- 1dichloromethyl- 3,5-bis(trifluoromethyl)phenyl- 165 methyl- 2dichloromethyl- 3,5-bis(trifluoromethyl)phenyl- 166 chloro- 2dichloromethyl- 3,5-bis(trifluoromethyl)phenyl- 167 bromo- 2dichloromethyl- 3,5-bis(trifluoromethyl)phenyl- 168 trifluoromethyl- 2dichloromethyl- 3,5-bis(trifluoromethyl)phenyl- 169 methyl- 0trifluoromethyl- 3-(trifluoromethyl)phenyl- 170 chloro- 0trifluoromethyl- 3-(trifluoromethyl)phenyl- 171 bromo- 0trifluoromethyl- 3-(trifluoromethyl)phenyl- 172 trifluoromethyl- 0trifluoromethyl- 3-(trifluoromethyl)phenyl- 173 methyl- 1trifluoromethyl- 3-(trifluoromethyl)phenyl- 174 chloro- 1trifluoromethyl- 3-(trifluoromethyl)phenyl- 175 bromo- 1trifluoromethyl- 3-(trifluoromethyl)phenyl- 176 trifluoromethyl- 1trifluoromethyl- 3-(trifluoromethyl)phenyl- 177 methyl- 2trifluoromethyl- 3-(trifluoromethyl)phenyl- 178 chloro- 2trifluoromethyl- 3-(trifluoromethyl)phenyl- 179 bromo- 2trifluoromethyl- 3-(trifluoromethyl)phenyl- 180 trifluoromethyl- 2trifluoromethyl- 3-(trifluoromethyl)phenyl- 181 methyl- 0dichloromethyl- 3-(trifluoromethyl)phenyl- 182 chloro- 0 dichloromethyl-3-(trifluoromethyl)phenyl- 183 bromo- 0 dichloromethyl-3-(trifluoromethyl)phenyl- 184 trifluoromethyl- 0 dichloromethyl-3-(trifluoromethyl)phenyl- 185 methyl- 1 dichloromethyl-3-(trifluoromethyl)phenyl- 186 chloro- 1 dichloromethyl-3-(trifluoromethyl)phenyl- 187 bromo- 1 dichloromethyl-3-(trifluoromethyl)phenyl- 188 trifluoromethyl- 1 dichloromethyl-3-(trifluoromethyl)phenyl- 189 methyl- 2 dichloromethyl-3-(trifluoromethyl)phenyl- 190 chloro- 2 dichloromethyl-3-(trifluoromethyl)phenyl- 191 bromo- 2 dichloromethyl-3-(trifluoromethyl)phenyl- 192 trifluoromethyl- 2 dichloromethyl-3-(trifluoromethyl)phenyl-Table 289

-   Table 289 provides 192 compounds of formula IA wherein R1 and R2    together represent the ring fragment (CH2)3, Y1-Y2-Y3 is —C═N—O—, A2    is CH, A3 is CH, A4 is CH, and R5b, n, R3 and R4 are as defined in    Table Q.    Table 290-   Table 290 provides 192 compounds of formula IA wherein R1 and R2    together represent the ring fragment (CH2)4, Y1-Y2-Y3 is —C═N—O—, A2    is CH, A3 is CH, A4 is CH, and R5b, n, R3 and R4 are as defined in    Table Q.    Table 291-   Table 291 provides 192 compounds of formula IA wherein R1 and R2    together represent the ring fragment (CH2)5, Y1-Y2-Y3 is —C═N—O—, A2    is CH, A3 is CH, A4 is CH, and R5b, n, R3 and R4 are as defined in    Table Q.    Table 292-   Table 292 provides 192 compounds of formula IA wherein R1 and R2    together represent the ring fragment (CH2)20(CH2)2, Y1-Y2-Y3 is    —C═N—O—, A2 is CH, A3 is CH, A4 is CH, and R5b, n, R3 and R4 are as    defined in Table Q.    Table 293-   Table 293 provides 192 compounds of formula IA wherein R1 and R2    together represent the ring fragment (CH2)3, Y1-Y2-Y3 is —C═N—CH2-,    A2 is CH, A3 is CH, A4 is CH, and R5b, n, R3 and R4 are as defined    in Table Q.    Table 294-   Table 294 provides 192 compounds of formula IA wherein R1 and R2    together represent the ring fragment (CH2)4, Y1-Y2-Y3 is —C═N—CH2-,    A2 is CH, A3 is CH, A4 is CH, and R5b, n, R3 and R4 are as defined    in Table Q.    Table 295-   Table 295 provides 192 compounds of formula IA wherein R1 and R2    together represent the ring fragment (CH2)5, Y1-Y2-Y3 is —C═N—CH2-,    A2 is CH, A3 is CH, A4 is CH, and R5b, n, R3 and R4 are as defined    in Table Q.    Table 296-   Table 296 provides 192 compounds of formula IA wherein R1 and R2    together represent the ring fragment (CH2)20(CH2)2, Y1-Y2-Y3 is    —C═N—CH2-, A2 is CH, A3 is CH, A4 is CH, and R5b, n, R3 and R4 are    as defined in Table Q.    Table 297-   Table 297 provides 192 compounds of formula IA wherein R1 and R2    together represent the ring fragment (CH2)3, Y1-Y2-Y3 is    —N—CH2-CH2-, A2 is CH, A3 is CH, A4 is CH, and R5b, n, R3 and R4 are    as defined in Table Q.    Table 298-   Table 298 provides 192 compounds of formula IA wherein R1 and R2    together represent the ring fragment (CH2)4, Y1-Y2-Y3 is    —N—CH2-CH2-, A2 is CH, A3 is CH, A4 is CH, and R5b, n, R3 and R4 are    as defined in Table Q.    Table 299-   Table 299 provides 192 compounds of formula IA wherein R1 and R2    together represent the ring fragment (CH2)5, Y1-Y2-Y3 is    —N—CH2-CH2-, A2 is CH, A3 is CH, A4 is CH, and R5b, n, R3 and R4 are    as defined in Table Q.    Table 300-   Table 300 provides 192 compounds of formula IA wherein R1 and R2    together represent the ring fragment (CH2)20(CH2)2, Y1-Y2-Y3 is    —N—CH2-CH2-, A2 is CH, A3 is CH, A4 is CH, and R5b, n, R3 and R4 are    as defined in Table Q.    Table 301-   Table 301 provides 192 compounds of formula IA wherein R1 and R2    together represent the ring fragment (CH2)3, Y1-Y2-Y3 is —C═CH—O—,    A2 is CH, A3 is CH, A4 is CH, and R5b, n, R3 and R4 are as defined    in Table Q.    Table 302-   Table 302 provides 192 compounds of formula IA wherein R1 and R2    together represent the ring fragment (CH2)4, Y1-Y2-Y3 is —C═CH—O—,    A2 is CH, A3 is CH, A4 is CH, and R5b, n, R3 and R4 are as defined    in Table Q.    Table 303-   Table 303 provides 192 compounds of formula IA wherein R1 and R2    together represent the ring fragment (CH2)5, Y1-Y2-Y3 is —C═CH—O—,    A2 is CH, A3 is CH, A4 is CH, and R5b, n, R3 and R4 are as defined    in Table Q.    Table 304-   Table 304 provides 192 compounds of formula IA wherein R1 and R2    together represent the ring fragment (CH2)20(CH2)2, Y1-Y2-Y3 is    —C═CH—O—, A2 is CH, A3 is CH, A4 is CH, and R5b, n, R3 and R4 are as    defined in Table Q.    Table 305-   Table 305 provides 192 compounds of formula IA wherein R1 and R2    together represent the ring fragment (CH2)3, Y1-Y2-Y3 is —C═N—S—, A2    is CH, A3 is CH, A4 is CH, and R5b, n, R3 and R4 are as defined in    Table Q.    Table 306-   Table 306 provides 192 compounds of formula IA wherein R1 and R2    together represent the ring fragment (CH2)4, Y1-Y2-Y3 is —C═N—S—, A2    is CH, A3 is CH, A4 is CH, and R5b, n, R3 and R4 are as defined in    Table Q.    Table 307-   Table 307 provides 192 compounds of formula IA wherein R1 and R2    together represent the ring fragment (CH2)5, Y1-Y2-Y3 is —C═N—S—, A2    is CH, A3 is CH, A4 is CH, and R5b, n, R3 and R4 are as defined in    Table Q.    Table 308-   Table 308 provides 192 compounds of formula IA wherein R1 and R2    together represent the ring fragment (CH2)20(CH2)2, Y1-Y2-Y3 is    —C═N—S—, A2 is CH, A3 is CH, A4 is CH, and R5b, n, R3 and R4 are as    defined in Table Q.    Table 309-   Table 309 provides 192 compounds of formula IA wherein R1 and R2    together represent the ring fragment (CH2)3, Y1-Y2-Y3 is —C═CH—S—,    A2 is CH, A3 is CH, A4 is CH, and R5b, n, R3 and R4 are as defined    in Table Q.    Table 310-   Table 310 provides 192 compounds of formula IA wherein R1 and R2    together represent the ring fragment (CH2)4, Y1-Y2-Y3 is —C═CH—S—,    A2 is CH, A3 is CH, A4 is CH, and R5b, n, R3 and R4 are as defined    in Table Q.    Table 311-   Table 311 provides 192 compounds of formula IA wherein R1 and R2    together represent the ring fragment (CH2)5, Y1-Y2-Y3 is —C═CH—S—,    A2 is CH, A3 is CH, A4 is CH, and R5b, n, R3 and R4 are as defined    in Table Q.    Table 312-   Table 312 provides 192 compounds of formula IA wherein R1 and R2    together represent the ring fragment (CH2)20(CH2)2, Y1-Y2-Y3 is    —C═CH—S—, A2 is CH, A3 is CH, A4 is CH, and R5b, n, R3 and R4 are as    defined in Table Q.

Compounds of formula I include at least one chiral centre and may existas compounds of formula I* or compounds of formula I**.

Generally compounds of formula I** are more biologically active thancompounds of formula I*. The invention includes mixtures of compounds I*and I** in any ratio e.g. in a molar ratio of 1:99 to 99:1, e.g. 10:1 to1:10, e.g. a substantially 50:50 molar ratio. In an enantiomerically (orepimerically) enriched mixture of formula I**, the molar proportion ofcompound I** compared to the total amount of both enantiomers is forexample greater than 50%, e.g. at least 55, 60, 65, 70, 75, 80, 85, 90,95, 96, 97, 98, or at least 99%. Likewise, in enantiomerically (orepimerically) enriched mixture of formula I*, the molar proportion ofthe compound of formula I* compared to the total amount of bothenantiomers (or epimerically) is for example greater than 50%, e.g. atleast 55, 60, 65, 70, 75, 80, 85, 90, 95, 96, 97, 98, or at least 99%.Enantiomerically (or epimerically) enriched mixtures of formula I** arepreferred. Each compound disclosed in Tables 1 to 312 represents aspecific disclosure of a compound according to formula I*, as well as aspecific disclosure of a compound according to formula I**.

Compounds of formula Int-I include at least one chiral centre and mayexist as compounds of formula Int-I* or compounds of formula Int-I**.

The invention includes mixtures of compounds Int-I* and Int-I** in anyratio e.g. in a molar ratio of 1:99 to 99:1, e.g. 10:1 to 1:10, e.g. asubstantially 50:50 molar ratio. In an enantiomerically (orepimerically) enriched mixture of formula Int-I**, the molar proportionof compound Int-I** compared to the total amount of both enantiomers isfor example greater than 50%, e.g. at least 55, 60, 65, 70, 75, 80, 85,90, 95, 96, 97, 98, or at least 99%. Likewise, in enantiomerically (orepimerically) enriched mixture of formula Int-I*, the molar proportionof the compound of formula Int-I* compared to the total amount of bothenantiomers (or epimerically) is for example greater than 50%, e.g. atleast 55, 60, 65, 70, 75, 80, 85, 90, 95, 96, 97, 98, or at least 99%.Enantiomerically (or epimerically) enriched mixtures of formula Int-I**are preferred.

The compounds of the invention may be made by a variety of methods asshown in the following Schemes.

1) Compounds of formula (IA) wherein n is 1 or 2, can be prepared byoxidation of compound of formula (III). Such reactions can be carriedout by treatment with an oxidising reagent, such as potassiumpermanganate, 3-chloroperoxybenzoic acid (“MCPBA”), sodiumperiodate/ruthenium(II) oxide, hydrogen peroxide, oxone and sodiumhypochlorite. One equivalent of oxidising reagent is required to conventa sulfide to a sulfoxide, or a sulfoxide to a sulfone. Two equivalentsof oxidising reagent are required to convent a sulfide to a sulfone.Preferred solvents are ethanol, methanol, tetrahydrofuran, dioxane,1,2-dimethoxyethane, ethyl acetate, toluene, dichloromethane and water,or mixtures thereof. The reaction is optionally carried out in thepresence of a base, for example a carbonate, such as sodium hydrogencarbonate. The reaction is carried out at a temperature of from 0° C. to100° C., preferably from 15° C. to 30° C., in particular at ambienttemperature.

2) Compounds of formula (III) can be prepared by reacting anintermediate of formula (II) wherein X^(B) is a leaving group, forexample a halogen, such as fluoro, chloro or bromo, with a mercaptan offormula (IV). Such reactions can be carried out in the presence of abase such as an amine or a carbonate, for example potassium or cesiumcarbonate in solvents such as acetonitrile, dimethylformamide,dimethylsulfoxide, dimethylacetamide at a temperature of from 0° C. to150° C., preferably from 25° C. to 100° C.

3) Compounds of formula (II) can be obtained using a variety of methods,for example as described in WO09080250. Compounds of formula (IV) areeither known compounds, such as 1-mercapto-metanesulfonamide (CAS207517-20-2) or can be prepared using known methods by the personskilled in the art.

4) Alternatively, compounds of formula (III) can be prepared byalkylation of an intermediate of formula (V) with a reagent of formula(VI) wherein Hal is chloro, bromo, or iodo. Such reactions can becarried out according to well established methods, described for examplein Journal of Medicinal Chemistry, 36(15), 2134-41; 1993. Compounds offormula (VI) are either known compounds, such as1-chloro-methanesulfonamide (CAS 21335-43-3), or can be prepared byknown methods to the person skilled in the art.

5) Compounds of formula (V) can be prepared by reaction of anintermediate of formula (II) wherein X^(B) is a halogen, such as chloro,bromo, iodo and a transition metal catalyst, such as copper, nickel andpalladium, a sulfur source such as sulfur, thiourea, and alkalithiosulfate. Such reactions can be carried out according to wellestablished methods, described for example in U.S. 5338886 (Ni andthiourea), Tetrahedron Letters (2011), 52, 205-208 (palladium andthiourea) and Chinese Journal of Chemistry (2010), 28, 1441-1443 (copperand thioruea). Alternatively compounds of formula (VI) can be preparedby reaction of an intermediate of formula (II) wherein X^(B) is ahalogen, such as fluoro and chloro and an excess of alkali alkylthiolate, such as sodium thiolate at a temperature between 50° C. and a180° C. This reaction can be carried out, as described for example inSynthesis (1983), (9), 751-5.

6) Compounds of formula (VII), which can be prepared according to themethods described in Schemes 1-2 from (XV) or (X) , may be converted tocompounds of formula (IX) by reaction with a ketone of formula (XVIII)according to methods described for example in WO2009/080250.

7) Subsequently, compounds of formula (IX) can be converted intocompounds of formula (IA) by treatment with hydroxylamine, a base and aphase transfer catalyst, as described for example in WO09080250.

8) Compounds of formula (IA) can be obtained as an enantiomericallyenriched mixture (the stereocentre indicated by *) either by chiralseparation of the racemic compound or by use of a chiral catalyst in theas shown on Scheme 4. Such catalysts can for example be a chiral phasetransfer catalyst, preferably a quinine derivative, for example acompound of formula XI.

wherein Z is optionally substituted aryl or optionally substitutedheteroaryl, W is ethyl or vinyl, and X is an anion, preferably a halogenanion, more preferably chloride or bromide. See for exampleWO2011/104089.

9) Compounds of formula (IA) wherein Y₁—Y₂—Y₃ is C═N—CH₂, C═N—S, C═CH—O,or N—CH₂—CH₂ can be similarly obtained as described on Scheme 5, usingthe same methods as those described under Scheme 1. See alsoWO2011/154555. Compounds of formula (XII) wherein Y₁--Y₂—Y₃ is C═N—CH₂can be prepared for example as described in WO2009/072621. Compounds offormula (XII) wherein Y₁—Y₂—Y₃ is N—CH₂—CH₂ can be prepared for exampleas described in WO2008/128711. Compounds of formula (XII) whereinY₁—Y₂—Y₃ is C═CH—O can be prepared for example as described in WO2011101229.

10) Compounds of formula (XII) Y₁—Y₂—Y₃ is C═N—CH₂, C═CH—O, C═N—S, orN—CH₂—CH₂ may also be similarly converted into compounds of formula(XIII) as described on Scheme 6, using the same methods as thosedescribed under Scheme 2.

11) Compounds of formula (XVII) wherein R¹¹ is C₁-C₆alkyl or C₁-C₆alkyloptionally substituted by an aryl, can be prepared by reacting anintermediate of formula (XV) wherein X^(B) is a leaving group, forexample a halogen, such as fluoro, chloro or bromo, with a mercaptan offormula (XVI) wherein R¹¹ is C₁-C₆alkyl or C₁-C₆alkyl optionallysubstituted by an aryl, for example tert-butyl. Such reactions can becarried out in the presence of a base such as an amine or a carbonate,for example potassium or cesium carbonate in solvents such asacetonitrile, dimethylformamide, dimethylsulfoxide, dimethylacetamide ata temperature of from 0° C. to 150° C., preferably from 25° C. to 100°C. Examples of such reactions can be found in Synlett 2006, 8,1255-1259, and specific examples are described in the experimentalsection. Alternatively, the reaction can be carried out in the presenceof a catalyst, for a example a palladium catalyst, and a ligand, forexample a phosphine ligand in a solvent such as tetrahydrofuran,dioxane, 1,2-dimethoxyethane, ethyl acetate, or toluene at a temperatureof from 0° C. to 150° C., preferably from 80° C. to 130° C. Thisreaction can be carried out under microwave irradiation, as describedfor example in WO2007/102059, and specific examples are described in theexperimental section.

12) Compounds of formula (XVII) wherein R¹¹ is C₁-C₆alkyl or C₁-C₆alklyoptionally substituted by an aryl, may be converted to compounds offormula (XVIII) wherein R¹¹ is C₁-C₆alkyl or C₁-C₆alkyl optionallysubstituted by an aryl, by reaction with a ketone of formula (VIII)according to methods described for example in WO2009/080250.

13) Subsequently, compounds of formula (XVIII) wherein R¹¹ is C₁-C₆alkylor C₁-C₆alkyl optionally substituted by an aryl,can be converted intocompounds of formula (XIX) wherein R¹¹ is C₁-C₆alky or C₁-C₆alkyoptionally substituted by an aryl, by treatment with hydroxylamine, abase and a phase transfer catalyst, as described for example inWO2009/080250.

14) Subsequently, compounds of formula (XIX) wherein R¹¹ is C₁-C₆alkylor C₁-C₆alkyl optionally substituted by an aryl, can be converted intocompounds of formula (V). Such reactions can be carried out in thepresence of an acid, e.g. a Lewis acid such as an sulfonic acid,carboxylic acid for example methylsulfonic acid, paratoluenesulfonicacid, trifluoroacetic acid, aluminum trichloride or mercury(II) acetatein solvents such as acetic acid, trifluoroacetic acid, toluene,dichloromethane, water, at a temperature of from −78° C. to 150° C.,preferably from 0° C. to 110° C. Examples of such reactions can be foundin Organometallics, 2007, 26, 897-909 and Chemical Communications 2009,5236-5238, and specific examples are described in the experimentalsection.

15) Compounds of formula (XVIII) wherein R¹¹ is C₁-C₆alkyl or C₁-C₆alkyloptionally substituted by an aryl, can be converted into compounds offormula (XIX) e.g. stereoselectively (the stereocentre indicated by *)wherein R¹¹ is C₁-C₆alkyl or C₁-C₆alkyl optionally substituted by anaryl, by treatment with hydroxylamine, a base and a phase transfercatalyst, as described for example in WO2009/080250.

16) Compounds of formula (XX) wherein Y₁—Y₂—Y₃ is C═N—CH₂, C═CH—O,C═N—S, or N—CH₂—CH₂ may also be similarly converted into compounds offormula (XIV) as described under Scheme 9, using the same methods asthose described under Scheme 2.

17) Compounds of formula (XXI) wherein X¹ is halogen such as, chloro,bromo, or iodo, or a sulfonate ester such as triflate or mesylate mayalso be similarly converted into compounds of formula (XXII) asdescribed under Scheme 10 by reaction of a pyrrolidine of formula(XXIII) in presence of a base, such as alkali metal alkoxide, alkaliphosphate or alkali carbonate, and a palladium or copper catalyst. Thereaction is carried out at a temperature of from 0° C. to 200° C.,preferably from 20° C. to 160° C. The equivalents of base use can varyfrom 0.1 to 10 equivalents, preferably from 1 to 4 equivalents.

In scheme 11 and following schemes, Ar stands for group Ar1 or group Ar2or group Ar3 or group Ar4

18) Compounds of formula (XXVI) can be prepared by reacting a compoundof formula (XXV) with the vinyl compound of formula (XXIV) optionally inthe presence of a suitable solvent, for example N,N-dimethylformamide,xylene, toluene, chlorobenzene or dichlorobenzene. The reaction can beperformed under microwave heating preferably at temperatures up to 200°C. and preferably under neat conditions using a large excess of thecompound of formula XXIV (e.g. 40 equivalents). Vinyl compounds offormula (XXIV) are commercially available or can be made by methodsknown to a person skilled in the art. Compounds of formula (XXV) can bemade by methods known to a person skilled in the art, as described forexample in Journal of Organic Chemistry (1981), 46(4), 771.

19) Compounds of formula (XXIX) wherein Ar is as defined under Scheme 11and R³ and R⁴ are as defined for compounds (I) and Z¹ is hydrogen,halogen, cyano, C₁-C₈alkyl, aryl-C₁-C₄alkylene-, C₁-C₈alkylcarbonyl-,arylsulfonyl- or arylthio-, can be obtained by reacting an unsaturatedketone of formula (XXVII) with a sulfur nucleophile, such as thioaceticacid, hydrogen sulfide, sodium sulfide, ammonium sulfide, thiourea,benzylmercaptan, sodium benzenethiosulfonate, sodium thiomethoxide ortert-butyl mercaptan. Such reactions can be performed optionally in thepresence of a base, such as sodium hydroxide, sodium ethoxide, sodiummethoxide, sodium tert-butoxide or potassium hydroxide. Such reationscan also be performed in the presence of an acid, for examplep-toluenesulfonic acid, hydrochloric acid, acetic acid, in a solvent,such as methanol, ethanol, N,N-dimethylformamide, toluene,dichloromethane, ethyl acetate, acetonitrile or chlorobenzene or water,or mixtures thereof, at a temperature of from 0° C. to 100° C.,preferably from ambient temperature to 80° C. Such conditions aredescribed, for example, in Journal of the American Chemical Society(1949), 71, 3554-5 or in Tetrahedron: Asymmetry (2003), 14(1), 113-117and Journal of Organic Chemistry (1996), 61, 1986.

20) Compounds of formula (XXVIII) wherein Ar is as defined under Scheme11 and R³ and R⁴ are as defined for compounds (I) and Z³ is thiol oraryl substituted C₁-C₈alkylsulfinyl-, can be made by reaction of theketone of formula (XXVII) with an amine, such astriphenylmethanesulfenamide. Such reactions are usually carried out inthe presence of an acid, for example p-toluenesulfonic acid,hydrochloric acid, acetic acid, optionally in the presence of a solvent,for example an alcohol, such as methanol or ethanol, or toluene,dichloromethane, water, or mixtures thereof. The reaction can be carriedour in the presence or the absence of a dehydrating agent, such asanhydrous magnesium sulfate or molecular sieves. It can also be perfomedusing a Dean Stark or Soxhlet apparatus that enables a constant removalof the water formed during the reaction. The reaction is carried out ata temperature of from 0° C. to 100° C., preferably from 15° C. to 30°C., in particular at ambient temperature.

21) Compounds of formula (XXX) wherein Ar is as defined under Scheme 11and R³ and R⁴ are as defined for compounds (I) and Z² is hydrogen orhydroxyl or C₁-C₈alkoxy- or C₁-C₈alkylsulfonyloxy- orC₁-C₈arylsulfonyloxy- or aryl-C₁-C₄alkylene-or aryl, can be made byreaction of the ketone of formula (XXIX) with an amine, such ashydroxylamine hydrochloride, methoxylamine or ammonia. Such reactionsare carried out in the presence of a base, for example an organic base,such as triethylamine or sodium acetate, or an inorganic base, such assodium hydrogen carbonate, optionally in the presence of a solvent, forexample an alcohol, such as methanol or ethanol, or water, or mixturesthereof. Such reactions can also be carried out in the presence of anacid or not, for example p-toluenesulfonic acid, hydrochloric acid,acetic acid, optionnally in the presence of a solvent, for example analcohol, such as methanol or ethanol, or toluene, dichloromethane,water, or mixtures thereof. The reaction can be carried our in thepresence or the absence of a dehydrating agent, such as anhydrousmagnesium sulfate or molecular sieves. It can also be perfomed using aDean Stark or Soxhlet apparatus that enables a constant removal of thewater formed during the reaction. The reaction is carried out at atemperature of from 0° C. to 100° C., preferably from 15° C. to 30° C.,in particular at ambient temperature.

22) Compounds of formula (XXVI) can be obtained by cyclising a compoundof formula (XXVI) wherein Z³ is thiol. Such reactions are usuallycarried out in the presence of an acid or not, for examplep-toluenesulfonic acid, optionnally in the presence of a solvent, forexample dichloroethane, methanol, ethanol, toluene, dichloromethane orchlorobenzene.The reaction is carried out at a temperature of from 0° C.to 200° C., preferably from 25° C. to 100° C. Alternatively, compoundsof formula (XXVI) can be obtained by cyclising a compound of formula(XXVIII) wherein Z³ is aryl substituted C₁-C₈alkylsulfinyl-. Suchreactions are usually carried out in the presence of an acid or not, forexample p-toluenesulfonic acid, trifluoroacetic acid or hydrochloricacid, optionnally in the presence of a solvent, for exampledichloroethane, methanol, ethanol, toluene, dichloromethane orchlorobenzene.The reaction is carried out at a temperature of from 0° C.to 200° C., preferably from 25° C. to 100° C. Such reactions usuallyinvolve first the deprotection of the thiol to give a compound offormula (XXVIII) wherein Z³ is thiol, followed by the cyclization.

23) Compounds of formula (XXVI) can be obtained from compound of formula(XXX) wherein Z¹ is hydrogen or C₁-C₈alkyl or aryl-C₁-C₄alkylene-orC₁-C₈alkylcarbonyl- or arylsulfonyl- or arylthio-, and Z² is hydrogen orhydroxyl or C₁-C₈alkoxy- or C₁-C₈alkylsulfonyloxy- orC₁-C₈arylsulfonyloxy- or aryl-C₁-C₄alkylene-or aryl. Such reactionsusually involve the deprotection of Z¹ and of Z² or of both groups. Thereaction can then involve the following intermediates:

Depending on the nature of Z¹ and Z², the deprotection conditions aredifferent and can be made by methods known to a person skilled in theart or as described in T. W. Green, P. G. M. Wuts, Protective Groups inOrganic Synthesis, Wiley-Interscience, New York, 1999, 564-566, 740-743.

24) Compounds of formula (XXVI) can be obtained from compound of formula(XXXa) from an oxidation reaction. Such reactions are usually carriedout in the presence of an oxidant, for example iodine, bromine, thionylchloride, Bis(trifluoroacetoxy)iodobenzene; The reaction can be carriedour in the presence of an acid, such as trifluoroacetic acid or aceticacid, optionnally in the presence of a solvent, for exampledichloroethane, dimethylsulfoxide, N,N-dimethylformamide, methanol,ethanol, toluene, dichloromethane, ethyl acetate or chlorobenzene. Thereaction is carried out at a temperature of from 0° C. to 200° C.,preferably from 25° C. to 100° C. Such transformations, includingreaction conditions and suitable catalyst, are described in Journal ofthe Chemical Society, Perkin Transactions 1: Organic and Bio-OrganicChemistry (1972-1999) (1985), (1), 153-7 and Organic Letters (2006),8(21), 4811-4813. Similarly, compounds of formula (XXVI) can be obtainedfrom a compound of formula (XXXb) wherein Z¹ is arylsulfonyl- orarylthio-, by an oxidation reaction as described in Journal of OrganicChemistry (1990), 55(13), 4156-62.

25) Compounds of formula (XXVI) can be obtained from compound of formula(XXXc) wherein Z² is C₁-C₈alkoxy-. Such reactions are usually carriedout in the presence of a copper (I) reagent, suchcopper-3-methylsalicylate. The reaction can be carried out in thepresence of a solvent, for example dichloroethane, dimethylsulfoxide,N,N-dimethylformamide, methanol, ethanol, toluene, dichloromethane,ethyl acetate or chlorobenzene. The reaction is carried out at atemperature of from 0° C. to 200° C., preferably from 25° C. to 100° C.,or under microwave heating conditions. Such transformations aredescribed in Journal of the American Chemical Society (2011), 133,6403-6410.

26) Alternatively, compounds of formula (XXVI) can be obtained directlyfrom a compound of formula (XXIX) wherein Z¹ is hydrogen. Such reactionsare usually carried out in the presence chloramines formed in situ fromammonia and chlorine or sodium hypochlorite or hypochlorous acid,optionally in the presence of a solvent, for example dichloroethane,methanol, ethanol, toluene, dichloromethane or chlorobenzene. Thereaction is carried out at a temperature of from −80° C. to 40° C.,preferably below −40° C.

27) Alternatively, compounds of formula (XXVI) can be obtained directlyfrom a compound of formula (XXIX) wherein Z¹ is halogen, cyano,arylsulfonyl- or arylthio-. Such reactions are usually carried out inthe presence ammonia, optionally in the presence of a solvent, forexample dichloroethane, tetrahydrofuran, methanol, ethanol, toluene,dichloromethane or chlorobenzene. The reaction is carried out at atemperature of from −80° C. to 80° C.

28) Alternatively, compounds of formula (XXVI) can be obtained directlyfrom a compound of formula (XXIX) wherein Z¹ is aryl-C₁-C₄alkylene. Suchreactions are usually carried out in two steps. The first step involvesthe treatment of a compound of formula (XXIX) wherein Z¹ isaryl-C₁-C₄alkylene with a suitable oxidant, such as sulfuryl chloride orchlorine, in the presence of a solvent, for example dichloroethane,methanol, ethanol, toluene, dichloromethane or chlorobenzene, to providea compound of formula (XXIX) wherein Z¹ is chlorine. The second stepthen involves the treatment a compound of formula (XXIX) wherein Z¹ ischlorine by an ammonia source, such as ammonia or ammonium bromide inthe presence of a base, in the presence of a solvent, for exampledichloroethane, methanol, ethanol, toluene, tetrahydrofuran,dichloromethane or chlorobenzene. Both steps are usually carried out ata temperature of from −80° C. to 80° C.

29) Alternatively, compounds of formula (XXVI) can be obtained directlyfrom a compound of formula (XXIX) wherein Z¹ is hydrogen. Such reactionsare usually carried out in the presence of a suitable nitrogenelectrophile, such as hydroxylamine-O-sulfonic acid. Such reactions arecarried out in the presence of a base, for example an organic base, suchas triethylamine or sodium acetate, or an inorganic base, such as sodiumhydrogen carbonate, sodium hydroxide or potassium hydroxide optionallyin the presence of a solvent, for example tetrahydrofuran, toluene, analcohol, such as methanol or ethanol, or water, or mixtures thereof. Thereaction is carried out at a temperature of from −80° C. to 80° C.

30) Compounds of formula (IA) can be obtained from compounds of formula(XXXI), (XXXII), or (XXXIII) as shown on Scheme 13 by standard methods,for example by alkylation with an electrophilic reagent R²-Hal,

31) Compounds of formula (XXXVII) wherein Ar is as defined under Scheme11 and R³ and R⁴ are as defined for compounds (I) can be obtained byreacting an unsaturated ketone of formula (XXXIV) with a sulfurnucleophile such as thioglycolate of type (A) wherein R³° is C₁-C₁₅alkyl or aryl in presence or absence of a base such as sodium hydroxide,sodium ethoxide, sodium methoxide, sodium tert-butoxide or potassiumhydroxide in a solvent, such as, acetonitrile, tetrahydrofuran,1,4-dioxane, toluene, dichloromethane, N,N-dimethylformamide, orchlorobenzene or water, or mixtures thereof, at a temperature of from 0°C. to 100° C., preferably from ambient temperature to 80° C. Suchconditions are described, for example, in European Journal of MedicinalChemistry (1992), 27, 633-9, to obtain compound of formula XXXV. Fromcompound XXXV the target molecule can be prepared by any of the twosequence via XXXIX or via XXXVI (as shown in scheme 14). In one sequencewhere compound of formulat XXXV can be dehydrated first to obtaincompound of formula XXXVIII which can then be put into standard esterhydrolysis condition known to person expert in the art to obtaincompound of formula XXXIX. This compound can then be subjected todecarboxylation under conditions like thermal heating or heating inpresence of a base to get compound of formula XXXVII. On the other handcompound of formula can also be converted to compound XXXVII in a twostep procedure, first by hydrolysis the ester under standard hydrolyticconditions to obtain compound of formula XXXVI followed by single stepdehydrative decarboxylation using sulphonyl chlorides first followed byheating the crude isolated material to obtain the compound of formulaXXXVII.

The compounds of formula (I) can be used to combat and controlinfestations of insect pests such as Lepidoptera, Diptera, Hemiptera,Thysanoptera, Orthoptera, Dictyoptera, Coleoptera, Siphonaptera,Hymenoptera and Isoptera and also other invertebrate pests, for example,acarine, nematode and mollusc pests. Insects, acarines, nematodes andmolluscs are hereinafter collectively referred to as pests. The pestswhich may be combated and controlled by the use of the compounsd of theinvention include those pests associated with agriculture (which termincludes the growing of crops for food and fiber products), horticultureand animal husbandry, companion animals, forestry and the storage ofproducts of vegetable origin (such as fruit, grain and timber); thosepests associated with the damage of man-made structures and thetransmission of diseases of man and animals; and also nuisance pests(such as flies). The compounds of the invention may be used for exampleon turf, ornamentals, such as flowers, shrubs, broad-leaved trees orevergreens, for example conifers, as well as for tree injection, pestmanagement and the like. Compositions comprising the compound of formulaI may be used on ornamental garden plants (e.g. flowers, shrubs,broad-leaved trees or evergreens), e.g. to control aphids, whitefly,scales, meelybug, beetles and caterpillars. Compositions comprising thecompound of formula I may be used on garden plants (e.g. flowers,shrubs, broad-leaved trees or evergreens), on indoor plants (e.g.flowers and shrubs) and on indoor pest e.g. to control aphids, whitefly,scales, meelybug, beetles and caterpillars.

Furthermore, the compounds of the invention may be effective againstharmful insects, without substantially imposing any harmful side effectsto cultivated plants. Application of the compounds of the invention mayincrease the harvest yields, and may improve the quality of theharvested material. The compounds of the invention may have favourableproperties with respect to amount appled, residue formulation,selectivity, toxicity, production methodology, high activity, widespectrum of control, safety, control of resistant organisms, e.g. peststhat are resistant to organic phosphorus agents and/or carbamate agents.

Examples of pest species which may be controlled by the compounds offormula (I) include: coleopterans, for example, Callosobruchuschinensis, Sitophilus zeamais, Tribolium castaneum, Epilachnavigintioctomaculata, Agriotes fuscicollis, Anomala rufocuprea,Leptinotarsa decemlineata, Diabrotica spp., Monochamus alternatus,Lissorhoptrus oryzophilus, Lyctus bruneus, Aulacophora femoralis;lepidopterans, for example, Lymantria dispar, Malacosoma neustria),Pieris rapae, Spodoptera litura, Mamestra brassicae, Chilosuppressalis), Pyrausta nubilalis, Ephestia cautella, Adoxophyes orana,Carpocapsa pomonella, Agrotisfucosa, Galleria mellonella, Plutellamaculipennis, Heliothis virescens, Phyllocnistis citrella; hemipterans,for example, Nephotettix cincticeps, Nilaparvata lugens, Pseudococcuscomstocki, Unaspis yanonensis, Myzus persicas, Aphis pomi, Aphisgossypii, Rhopalosiphum pseudobrassicas, Stephanitis nashi, Nezara spp.,Trialeurodes vaporariorm, Psylla spp.; thysanopterans, for example,Thrips palmi, Franklinella occidental; orthopterans, for example,Blatella germanica, Periplaneta americana, Gryllotalpa Africana, Locustamigratoria migratoriodes; isopterans, for example, Reticulitermessperatus, Coptotermes formosanus; dipterans, for example, Muscadomestica, Aedes aegypti, Hylemia platura, Culex pipiens, Anophelessinensis, Culex tritaeniorhynchus, Liriomyza trifolii; acari, forexample, Tetranychus cinnabarinus, Tetranychus urticae, Panonychuscitri, Aculops pelekassi, Tarsonemus spp.; nematodes, for example,Meloidogyne incognita, Bursaphelenchus lignicolus Mamiya et Kiyohara,Aphelenchoides besseyi, Heterodera glycines, Pratylenchus spp.

Examples of further pest species which may be controlled by thecompounds of formula (I) include: from the order of the Anoplura(Phthiraptera), for example, Damalinia spp., Haematopinus spp.,Linognathus spp., Pediculus spp., Trichodectes spp.; from the class ofthe Arachnida, for example, Acarus siro, Aceria sheldoni, Aculops spp.,Aculus spp., Amblyomma spp., Argas spp., Boophilus spp., Brevipalpusspp., Bryobia praetiosa, Chorioptes spp., Dermanyssus gallinae,Eotetranychus spp., Epitrimerus pyri, Eutetranychus spp., Eriophyesspp., Hemitarsonemus spp., Hyalomma spp., Ixodes spp., Latrodectusmactans, Metatetranychus spp., Oligonychus spp., Ornithodoros spp.,Panonychus spp., Phyllocoptruta oleivora, Polyphagotarsonemus latus,Psoroptes spp., Rhipicephalus spp., Rhizoglyphus spp., Sarcoptes spp.,Scorpio maurus, Stenotarsonemus spp., Tarsonemus spp., Tetranychus spp.,Vasates lycopersici; from the class of the Bivalva, for example,Dreissena spp.; from the order of the Chilopoda, for example, Geophilusspp., Scutigera spp.; from the order of the Coleoptera, for example,Acanthoscehdes obtectus, Adoretus spp., Agelastica alni, Agriotes spp.,Amphimallon solstitialis, Anobium punctatum, Anoplophora spp.,Anthonomus spp., Anthrenus spp., Apogonia spp., Atomaria spp., Attagenusspp., Bruchidius obtectus, Bruchus spp., Ceuthorhynchus spp., Cleonusmendicus, Conoderus spp., Cosmopolites spp., Costelytra zealandica,Curculio spp., Cryptorhynchus lapathi, Dermestes spp., Diabrotica spp.,Epilachna spp., Faustinus cubae, Gibbium psylloides, Heteronychusarator, Hylamorpha elegans, Hylotrupes bajulus, Hypera postica,Hypothenemus spp., Lachnosterna consanguinea, Leptinotarsa decemlineata,Lissorhoptrus oryzophilus, Lixus spp., Lyctus spp., Meligethes aeneus,Melolontha melolontha, Migdolus spp., Monochamus spp., Naupactusxanthographus, Niptus hololeucus, Oryctes rhinoceros, Oryzaephilussurinamensis, Otiorrhynchus sulcatus, Oxycetonia jucunda, Phaedoncochleariae, Phyllophaga spp., Popillia japonica, Premnotrypes spp.,Psylliodes chrysocephala, Ptinus spp., Rhizobius ventralis, Rhizoperthadominica, Sitophilus spp., Sphenophorus spp., Sternechus spp.,Symphyletes spp., Tenebrio molitor, Tribolium spp., Trogoderma spp.,Tychius spp., Xylotrechus spp., Zabrus spp.; from the order of theCollembola, for example, Onychiurus armatus; from the order of theDermaptera, for example, Forficula auricularia; from the order of theDiplopoda, for example, Blaniulus guttulatus; from the order of theDiptera, for example, Aedes spp., Anopheles spp., Bibio hortulanus,Calliphora erythrocephala, Ceratitis capitata, Chrysomyia spp.,Cochliomyia spp., Cordylobia anthropophaga, Culex spp., Cuterebra spp.,Dacus oleae, Dermatobia hominis, Drosophila spp., Fannia spp.,Gastrophilus spp., Hylemyia spp., Hyppobosca spp., Hypoderma spp.,Liriomyza spp., Lucilia spp., Musca spp., Nezara spp., Oestrus spp.,Oscinella frit, Pegomyia hyoscyami, Phorbia spp., Stomoxys spp., Tabanusspp., Tannia spp., Tipula paludosa, Wohlfahrtia spp.; from the class ofthe Gastropoda, for example, Anion spp., Biomphalaria spp., Bulinusspp., Deroceras spp., Galba spp., Lymnaea spp., Oncomelania spp.,Succinea spp.; from the class of the helminths, for example, Ancylostomaduodenale, Ancylostoma ceylanicum, Acylostoma braziliensis, Ancylostomaspp., Ascaris lubricoides, Ascaris spp., Brugia malayi, Brugia timori,Bunostomum spp., Chabertia spp., Clonorchis spp., Cooperia spp.,Dicrocoelium spp, Dictyocaulus filaria, Diphyllobothrium latum,Dracunculus medinensis, Echinococcus granulosus, Echinococcusmultilocularis, Enterobius vermicularis, Faciola spp., Haemonchus spp.,Heterakis spp., Hymenolepis nana, Hyostrongulus spp., Loa Loa,Nematodirus spp., Oesophagostomum spp., Opisthorchis spp., Onchocercavolvulus, Ostertagia spp., Paragonimus spp., Schistosomen spp.,Strongyloides fuelleborni, Strongyloides stercoralis, Stronyloides spp.,Taenia saginata, Taenia solium, Trichinella spiralis, Trichinellanativa, Trichinella britovi, Trichinella nelsoni, Trichinellapseudopsiralis, Trichostrongulus spp., Trichuris trichuria, Wuchereriabancrofti; ft may be furthermore possible to control protozoa, such asEimeria; from the order of the Heteroptera, for example, Anasa tristis,Antestiopsis spp., Blissus spp., Calocoris spp., Campylomma livida,Cavelerius spp., Cimex spp., Creontiades dilutus, Dasynus piperis,Dichelops furcatus, Diconocoris hewetti, Dysdercus spp., Euschistusspp., Eurygaster spp., Heliopeltis spp., Horcias nobilellus, Leptocorisaspp., Leptoglossus phyllopus, Lygus spp., Macropes excavatus, Miridae,Nezara spp., Oebalus spp., Pentomidae, Piesma quadrata, Piezodorus spp.,Psallus seriatus, Pseudacysta persea, Rhodnius spp., Sahlbergellasingularis, Scotinophora spp., Stephanitis nashi, Tibraca spp., Triatomaspp.; from the order of the Homoptera, for example, Acyrthosipon spp.,Aeneolamia spp., Agonoscena spp., Aleurodes spp., Aleurolobusbarodensis, Aleurothrixus spp., Amrasca spp., Anuraphis cardui,Aonidiella spp., Aphanostigma pini, Aphis spp., Arboridia apicalis,Aspidiella spp., Aspidiotus spp., Atanus spp., Aulaconthum solani,Bemisia spp., Brachycaudus helichrysii, Brachycolus spp., Brevicorynebrassicae, Calligypona manginata, Canneocephala fulgida, Ceratovacunalanigena, Cercopidae, Cenoplastes spp., Chaetosiphon fragaefolii,Chionaspis tegalensis, Chlorita onukii, Chromaphis juglandicola,Chrysomphalus ficus, Cicadulina mbila, Coccomytilus halli, Coccus spp.,Cryptomyzus ribis, Dalbulus spp., Dialeunodes spp., Diaphorina spp.,Diaspis spp., Dorsalis spp., Drosicha spp., Dysaphis spp., Dysmicoccusspp., Empoasca spp., Eniosoma spp., Erythnoneuna spp., Euscelisbilobatus, Geococcus coffeae, Homalodisca coagulata, Hyaloptenusarundinis, Icerya spp., Idiocenus spp., Idioscopus spp., Laodelphaxstniatellus, Lecanium spp., Lepidosaphes spp., Lipaphis erysimi,Macnosiphum spp., Mahanarva fimbriolata, Melanaphis sacchari,Metcalfiella spp., Metopolophium dinhodum, Monellia costalis,Monelliopsis pecanis, Myzus spp., Nasonovia ribisnigri, Nephotettixspp., Nilaparvata lugens, Oncometopia spp., Onthezia pnaelonga,Panabemisia mynicae, Paratrioza spp., Panlatonia spp., Pemphigus spp.,Peregrinus maidis, Phenacoccus spp., Phloeomyzus passeninii, Phorodonhumuli, Phylloxera spp., Pinnaspis aspidistrae, Planococcus spp.,Protopulvinania pyriformis, Pseudaulacaspis pentagona, Pseudococcusspp., Psylla spp., Ptenomalus spp., Pynilla spp., Quadnaspidiotus spp.,Quesada gigas, Rastrococcus spp., Rhopalosiphum spp., Saissetia spp.,Scaphoides titanus, Schizaphis graminum, Selenaspidus anticulatus,Sogata spp., Sogatella furcifera, Sogatodes spp., Stictocephala festina,Tenalaphana malayensis, Tinocallis caryaefoliae, Tomaspis spp.,Toxoptera spp., Tnialeunodes vaporariorum, Trioza spp., Typhlocyba spp.,Unaspis spp., Viteus vitifolii; from the order of the Hymenoptera, forexample, Dipnion spp., Hoplocampa spp., Lasius spp., Mono-moniumphanaonis, Vespa spp.; from the order of the Isopoda, for example,Armadillidium vulgane, Oniscus asellus, Poncellio scaben; from the orderof the Isoptena, for example, Reticulitermes spp., Odontotermes spp.;from the order of the Lepidoptera, for example, Acronicta major, Aedialeucomelas, Agnotis spp., Alabama argillacea, Anticarsia ssp., Barathrabrassicae, Bucculatrix thurberiella, Bupalus piniarius, Cacoecia podana,Capua reticulana, Carpocapsa pomonella, Cheimatobia brumata, Chilo ssp.,Choristoneura fumiferana, Clysia ambiguella, Cnaphalocerus ssp., Eariasinsulana, Ephestia kuehniella, Euproctis chrysorrhoea, Euxoa ssp.,Feltia ssp., Galleria mellonella, Helicoverpa ssp., Heliothis ssp.,Hofmannophila pseudospretella, Homona magnanima, Hyponomeuta padella,Laphygma ssp., Lithocolletis blancardella, Lithophane antennata,Loxagrotis albicosta, Lymantria ssp., Malacosoma neustria, Mamestrabrassicae, Mocis repanda, Mythimna separata, Oria ssp., Oulema oryzae,Panolis flammea, Pectinophora gossypiella, Phyllocnistis citrella,Pieris ssp., Plutella xylostella, Prodenia ssp., Pseudaletia ssp.,Pseudoplusia includens, Pyrausta nubilalis, Spodoptera ssp., Thermesiagemmatalis, Tinea pellionella, Tineola bisselliella, Tortrix viridana,Trichoplusia ssp.; from the order of the Orthoptera, for example, Achetadomesticus, Blatta orientalis, Blattella germanica, Gryllotalpa ssp.,Leucophaea maderae, Locusta ssp., Melanoplus ssp., Periplanetaamericana, Schistocerca gregaria; from the order of the Siphonaptera,for example, Ceratophyllus ssp., Xenopsylla cheopis. From the order ofthe Symphyla, for example, Scutigerella immaculata; from the order ofthe Thysanoptera, for example, Baliothrips biformis, Enneothripsflavens, Frankliniella ssp., Heliothrips ssp., Hercinothrips femoralis,Kakothrips ssp., Rhipiphorothrips cruentatus, Scirtothrips ssp.,Taeniothrips cardamoni, Thrips ssp.; from the order of the Thysanura,for example, Lepisma saccharina. The phytoparasitic nematodes include,for example, Anguina ssp., Aphelenchoides ssp., Belonoaimus ssp.,Bursaphelenchus ssp., Ditylenchus dipsaci, Globodera ssp.,Heliocotylenchus ssp., Heterodera ssp., Longidorus ssp., Meloidogynessp., Pratylenchus ssp., Radopholus similis, Rotylenchus ssp.,Trichodorus ssp., Tylenchorhynchus ssp., Tylenchulus ssp., Tylenchulussemipenetrans, Xiphinema ssp.

In particular, the compounds of the invention may be used to control thefollowing pest spcies:

Myzus persicae (aphid), Aphis gossypii (aphid), Aphis fabae (aphid),Lygus ssp. (capsids), Dysdercus ssp. (capsids), Nilaparvata lugens(planthopper), Nephotettixc incticeps (leafhopper), Nezara ssp.(stinkbugs), Euschistus ssp. (stinkbugs), Leptocorisa ssp. (stinkbugs),Frankliniella occidentalis (thrip), Thrips ssp. (thrips), Leptinotarsadecemlineata (Colorado potato beetle), Anthonomus grandis (boll weevil),Aonidiella ssp. (scale insects), Trialeurodes ssp. (white flies),Bemisia tabaci (white fly), Ostrinia nubilalis (European corn borer),Spodoptera littoralis (cotton leafworm), Heliothis virescens (tobaccobudworm), Helicoverpa armigera (cotton bollworm), Helicoverpa zea(cotton bollworm), Sylepta derogata (cotton leaf roller), Pierisbrassicae (white butterfly), Plutella xylostella (diamond back moth),Agrotis ssp. (cutworms), Chilo suppressalis (rice stem borer), Locustamigratoria (locust), Chortiocetes terminifera (locust), Diabrotica ssp.(rootworms), Panonychus ulmi (European red mite), Panonychus citri(citrus red mite), Tetranychus urticae (two-spotted spider mite),Tetranychus cinnabarinus (carmine spider mite), Phyllocoptruta oleivora(citrus rust mite), Polyphagotarsonemus latus (broad mite), Brevipalpusssp. (flat mites), Boophilus microplus (cattle tick), Dermacentorvariabilis (American dog tick), Ctenocephalides felis (cat flea),Liriomyza ssp. (leafminer), Musca domestica (housefly), Aedes aegypti(mosquito), Anopheles ssp. (mosquitoes), Culex ssp. (mosquitoes),Lucillia ssp. (blowflies), Blattella germanica (cockroach), Periplanetaamericana (cockroach), Blatta orientalis (cockroach), termites of theMastotermitidae (for example Mastotermes ssp.), the Kalotermitidae (forexample Neotermes ssp.), the Rhinotermitidae (for example Coptotermesformosanus, Reticulitermes flavipes, R. speratu, R. virginicus, R.hesperus, and R. santonensis) and the Termitidae (for exampleGlobitermes sulfureus), Solenopsis geminata (fire ant), Monomoriumpharaonis (pharaoh's ant), Damalinia ssp. and Linognathus ssp. (bitingand sucking lice), Meloidogyne ssp. (root knot nematodes), Globoderassp. and Heterodera ssp. (cyst nematodes), Pratylenchus ssp. (lesionnematodes), Rhodopholus ssp. (banana burrowing nematodes), Tylenchulusssp.(citrus nematodes), Haemonchus contortus (barber pole worm),Caenorhabditis elegans (vinegar eelworm), Trichostrongylus ssp. (gastrointestinal nematodes) and Deroceras reticulatum (slug).

The compound of formula I may be used for pest control on variousplants, including soybean (e.g. in some cases 10-70 g/ha), corn (e.g. insome cases 10-70 g/ha), sugarcane (e.g. in some cases 20-200 g/ha),alfalfa (e.g. in some cases 10-70 g/ha), brassicas (e.g. in some cases10-50 g/ha), oilseed rape (e.g. canola) (e.g. in some cases 20-70 g/ha),potatoes (including sweet potatoes) (e.g. in some cases 10-70 g/ha),cotton (e.g. in some cases 10-70 g/ha), rice (e.g. in some cases 10-70g/ha), coffee (e.g. in some 15 cases 30-150 g/ha), citrus (e.g. in somecases 60-200 g/ha), almonds (e.g. in some cases 40-180 g/ha), fruitingvegetables, cucurbits and pulses (e.g. tomatoes, pepper, chili,eggplant, cucumber, squash etc.) (e.g. in some cases 10-80 g/ha), tea(e.g. in some cases 20-150 g/ha), bulb vegetables (e.g. onion, leeketc.) (e.g. in some cases 30-90 g/ha), grapes (e.g. in some cases 30-180g/ha), pome fruit (e.g. apples, pears etc.) (e.g. in some cases 30-180g/ha), and stone fruit (e.g. pears, plums etc.) (e.g. in some cases30-180 g/ha).

The compounds of the invention may be used for pest control on variousplants, including soybean, corn, sugarcane, alfalfa, brassicas, oilseedrape (e.g. canola), potatoes (including sweet potatoes), cotton, rice,coffee, citrus, almonds, fruiting vegetables, cucurbits and pulses (e.g.tomatoes, pepper, chili, eggplant, cucumber, squash etc.), tea, bulbvegetables (e.g. onion, leek etc.), grapes, pome fruit (e.g. apples,pears etc.), stone fruit (e.g. pears, plums etc.), and cereals.

The compounds of the invention may be used on soybean to control, forexample, Elasmopalpus lignosellus, Diloboderus abderus, Diabroticaspeciosa, Trialeurodes ssp., Bemisia ssp., aphids, Sternechussubsignatus, Formicidae, Agrotis ypsilon, Julus ssp., Murgantia ssp.,Halyomorpha ssp., Thyanta ssp., Megascelis ssp., Procornitermes ssp.,Gryllotalpidae, Nezara viridula, Piezodorus ssp., Acrosternum ssp.,Neomegalotomus ssp., Cerotoma trifurcata, Popillia japonica, Edessassp., Liogenys fuscus, Euschistus heros, stalk borer, Scaptocoriscastanea, phyllophaga ssp., Migdolus ssp., Pseudoplusia includens,Anticarsia gemmatalis, Epinotia ssp., Rachiplusia ssp., Spodoptera ssp.,Bemisia tabaci, Tetranychus ssp., Agriotes ssp., Euschistus ssp. Thecompounds of the invention are preferably used on soybean to controlDiloboderus abderus, Diabrotica speciosa, Trialeurodes ssp., Bemisiassp., Nezara viridula, Piezodorus ssp., Acrosternum ssp., Cerotomatrifurcata, Popillia japonica, Euschistus heros, Scaptocoris castanea,phyllophaga ssp., Migdolus ssp., Agriotes ssp., Euschistus ssp.

The compounds of the invention may be used on corn to control, forexample, Euschistus heros, Euschistus ssp., Dichelops furcatus,Diloboderus abderus, Thyanta ssp., Elasmopalpus lignosellus, Halyomorphassp., Spodoptera frugiperda, Nezara viridula, Cerotoma trifurcata,Popillia japonica, Agrotis ypsilon, Diabrotica speciosa, aphids,Heteroptera, Procornitermes ssp., Scaptocoris castanea, Formicidae,Julus ssp., Dalbulus maidis, Diabrotica virgifera, Diabrotica ssp.,Mocis latipes, Bemisia tabaci, heliothis ssp., Tetranychus ssp., thripsssp., phyllophaga ssp., Migdolus ssp., scaptocoris ssp., Liogenysfuscus, Spodoptera ssp., Ostrinia ssp., Sesamia ssp., wireworms,Agriotes ssp., Halotydeus destructor. The compounds of the invention arepreferably used on corn to control Euschistus heros, Euschistus ssp.,Dichelops furcatus, Diloboderus abderus, Nezara viridula, Cerotomatrifurcata, Popillia japonica, Diabrotica speciosa, Diabroticavirgifera, Diabrotica ssp., Tetranychus ssp., Thrips ssp., Phyllophagassp., Migdolus ssp., Scaptocoris ssp., Agriotes ssp.

The compounds of the invention may be used on sugar cane to control, forexample, Sphenophorus ssp., termites, Migdolus ssp., Diloboderus ssp.,Telchin licus, Diatrea saccharalis, Mahanarva ssp., Mealybugs.

The compounds of the invention may be used on alfalfa to control, forexample, Hypera brunneipennis, Hypera postica, Colias eurytheme, Collopsssp., Empoasca solana, Epitrix ssp., Geocoris ssp., Lygus hesperus,Lygus lineolaris, Spissistilus ssp., Spodoptera ssp., Aphids,Trichoplusia ni. The compounds of the invention are preferably used onalfalfa to control Hypera brunneipennis, Hypera postica, Empoascasolana, Epitrix ssp., Lygus hesperus, Lygus lineolaris, Trichoplusia ni.

The compounds of the invention may be used on brassicas to control, forexample, Plutella xylostella, Pieris ssp., Mamestra ssp., Plusia ssp.,Trichoplusia ni, Phyllotreta ssp., Spodoptera ssp., Empoasca ssp.,thrips ssp., Delia ssp., Murgantia ssp., Trialeurodes ssp., Bemisiassp., Microtheca ssp., Aphids.The compounds of the invention arepreferably used on brassicas to control Plutella xylostella, Pierisssp., Plusia ssp., Trichoplusia ni, Phyllotreta ssp., Thrips ssp.

The compounds of the invention may be used on oil seed rape, e.g.canola, to control, for example, Meligethes ssp., Ceutorhynchus napi,Halotydeus destructor, Psylloides ssp.

The compounds of the invention may be used on potatoes, including sweetpotatoes, to control, for example, Empoasca ssp., Leptinotarsa ssp.,Diabrotica speciosa, Phthorimaea ssp., Paratrioza ssp., Maladeramatrida, Agriotes ssp., Aphids, wireworms. The compounds of theinvention are preferably used on potatoes, including sweet potatoes, tocontrol Empoasca ssp., Leptinotarsa ssp., Diabrotica speciosa,Phthorimaea ssp., Paratrioza ssp., Agriotes ssp.

The compounds of the invention may be used on cotton to control, forexample, Anthonomus grandis, Pectinophora ssp., heliothis ssp.,Spodoptera ssp., Tetranychus ssp., Empoasca ssp., Thrips ssp., Bemisiatabaci, Trialeurodes ssp., Aphids, Lygus ssp., phyllophaga ssp.,Scaptocoris ssp., Austroasca viridigrisea, Creontiades ssp., Nezarassp., Piezodorus ssp., Halotydeus destructor, Oxycaraenus hyalinipennis,Dysdercus cingulatus. The compounds of the invention are preferably usedon cotton to control Anthonomus grandis, Tetranychus ssp., Empoascassp., thrips ssp., Lygus ssp., phyllophaga ssp., Scaptocoris ssp.

The compounds of the invention may be used on rice to control, forexample, Leptocorisa ssp., Cnaphalocrosis ssp., Chilo ssp., Scirpophagassp., Lissorhoptrus ssp., Oebalus pugnax, Scotinophara ssp., Nephotettixmalayanus, Nephotettix nigropictus, Nephotettix parvus, Nephottetixvirescens, Nephotettix ssp., Mealybugs, Sogatella furcifera, Nilaparvatalugens, Orseolia ssp., Cnaphalocrocis medinalis, Marasmia ssp.,Stenchaetothrips biformis, Thrips ssp., Hydrellia philippina,Grasshoppers, Pomacea canaliculata, Scirpophaga innotata, Chilosuppressalis, Chilo auricilius, Chilo polychrysus, Sesamia inferens,Laodelphax striatellus, Nymphula depunctalis, Oulema oryzae, Stinkbugs.The compounds of the invention are preferably used on rice to controlLeptocorisa ssp., Lissorhoptrus ssp., Oebalus pugnax, Nephotettixmalayanus, Nephotettix nigropictus, Nephotettix parvus, Nephottetixvirescens, Nephotettix ssp., Sogatella furcifera, Stenchaetothripsbiformis, Thrips ssp., Hydrellia philippina, Grasshoppers, Pomaceacanaliculata, Scirpophaga innotata, Chilo suppressalis, Chilopolychrysus, Oulema oryzae.

The compounds of the invention may be used on coffee to control, forexample, Hypothenemus Hampei, Perileucoptera Coffeella, Tetranychusssp., Brevipalpus ssp., Mealybugs. The compounds of the invention arepreferably used on coffee to control Hypothenemus Hampei, PerileucopteraCoffeella.

The compounds of the invention may be used on citrus to control, forexample, Panonychus citri, Phyllocoptruta oleivora, Brevipalpus ssp.,Diaphorina citri, Scirtothrips ssp., Thrips ssp., Unaspis ssp.,Ceratitis capitata, Phyllocnistis ssp., Aphids, Hardscales, Softscales,Mealybugs. The compounds of the invention are preferably used on citrusto control Panonychus citri, Phyllocoptruta oleivora, Brevipalpus ssp.,Diaphorina citri, Scirtothrips ssp., thrips ssp., Phyllocnistis ssp.

The compounds of the invention may be used on almonds to control, forexample, Amyelois transitella, Tetranychus ssp.

The compounds of the invention may be used on fruiting vegetables,cucurbits and pulses, including tomatoes, pepper, chili, eggplant,cucumber, squash etc., to control, for example, Thrips ssp., Tetranychusssp., Polyphagotarsonemus ssp., Aculops ssp., Empoasca ssp., Spodopterassp., heliothis ssp., Tuta absoluta, Liriomyza ssp., Bernisia tabaci,Trialeurodes ssp., Aphids, Paratrioza ssp., Frankliniella occidentalis,Frankliniella ssp., Anthonomus ssp., Phyllotreta ssp., Amrasca ssp.,Epilachna ssp., Halyomorpha ssp., Scirtothrips ssp., Leucinodes ssp.,Neoleucinodes ssp. Maruca ssp., Fruit flies, Stinkbugs, Lepidopteras,Coleopteras. The compounds of the invention are preferably used onfruiting vegetables, cucurbits and pulses, including tomatoes, pepper,chili, eggplant, cucumber, squash etc., to control Thrips ssp.,Tetranychus ssp., Polyphagotarsonemus ssp., Aculops ssp., Empoasca ssp.,Spodoptera ssp., heliothis ssp., Tuta absoluta, Liriomyza ssp.,Paratrioza ssp., Frankliniella occidentalis, Frankliniella ssp., Amrascassp., Scirtothrips ssp., Leucinodes ssp., Neoleucinodes ssp.

The compounds of the invention may be used on tea to control, forexample, Pseudaulacaspis ssp., Empoasca ssp., Scirtothrips ssp.,Caloptilia theivora, Tetranychus ssp. The compounds of the invention arepreferably used on tea to control Empoasca ssp., Scirtothrips ssp.

The compounds of the invention may be used on bulb vegetables, includingonion, leek etc. to control, for example, Thrips ssp., Spodoptera ssp.,heliothis ssp. The compounds of the invention are preferably used onbulb vegetables, including onion, leek etc. to control Thrips ssp.

The compounds of the invention may be used on grapes to control, forexample, Empoasca ssp., Lobesia ssp., Eupoecilia ambiguella,Frankliniella ssp., Thrips ssp., Tetranychus spp., RhipiphorothripsCruentatus, Eotetranychus Willamettei, Erythroneura Elegantula,Scaphoides spp., Scelodonta strigicollis, Mealybugs. The compounds ofthe invention are preferably used on grapes to control Frankliniellaspp., Thrips spp., Tetranychus spp., Rhipiphorothrips Cruentatus,Scaphoides spp.

The compounds of the invention may be used on pome fruit, includingapples, pears etc., to control, for example, Cacopsylla spp., Psyllaspp., Panonychus ulmi, Cydia pomonella, Lepidopteras, Aphids,Hardscales, Softscales. The compounds of the invention are preferablyused on pome fruit, including apples, pears etc., to control acopsyllaspp., Psylla spp., Panonychus ulmi.

The compounds of the invention may be used on stone fruit to control,for example, Grapholita molesta, Scirtothrips spp., Thrips spp.,Frankliniella spp., Tetranychus spp., Aphids, Hardscales, Softscales,Mealybugs. The compounds of the invention are preferably used on stonefruit to control Scirtothrips spp., Thrips spp., Frankliniella spp.,Tetranychus spp.

The compounds of the invention may be used on cereals to control, forexample, Aphids, Stinkbugs, earthmites, Eurygaster integriceps, Zabrustenebrioides, Anisoplia austriaca, Chaetocnema aridula, Phyllotretaspp., Oulema melanopus, Oscinella spp., Delia spp., Mayetiola spp.,Contarinia spp., Cephus spp., Steneotarsonemus spp., Apamea spp.

In another embodiment compounds of formula I and mixtures of theinvention may be used on rice to control Baliothrips biformis (Thrips),Chilo spp. (e.g. Chilo polychrysus (Dark headed striped borer), Chilosuppressalis (Rice stemborer), Chilo indicus (Paddy stem borer), Chilopolychrysus (Dark-headed rice borer), Chilo suppressalis (Stripe stemborer)), Cnaphalocrocis medinalis (Rice leaf folder), Dicladispaarmigera (Hispa), Hydrellia philipina (Rice whorl-maggot), Laodelphaxspp. (Smaller brown planthopper) (e.g. Laodelphax striatellus), Lemaoryzae (Rice leafbeetle), Leptocorsia acuta (Rice bug), Leptocorsiaoratorius (rice bug), Lissorhoptrus oryzophilus (rice water weevil),Mythemina separata (armyworm), Nephottetix spp. (Green leafhopper) (e.g.Nephotettix cincticeps, Nephotettix malayanus, Nephotettix nigropictus,Nephotettix parvus, Nephottetix virescens), Nilaparvata lugens (BrownPlanthopper), Nymphula depunctalis (Rice caseworm), Orseolia oryzae(Rice Gall midge), Oulema oryzae (Rice leafbeetle), Scirpophagaincertulas (Yellow Stemborer), Scirpophaga innotata (White Stemborer),Scotinophara coarctata (Rice black bug), Sogaella frucifera(White-backed planthopper), Steneotarsonemus spinki.

The compounds of the invention may be used to control animal housingpests including: Ants, Bedbugs (adult), Bees, Beetles, Boxelder Bugs,Carpenter Bees, Carpet Beetles, Centipedes, Cigarette, Beetles, CloverMites, Cockroaches, Confused Flour Beetle, Crickets, Earwigs, Firebrats,Fleas, Flies, Lesser Grain Borers, Millipedes, Mosquitoes, Red FlourBeetles, Rice Weevils, Saw-toothed Grain Beetles, Silverfish, Sowbugs,Spiders, Termites, Ticks, Wasps, Cockroaches, Crickets, Flies, LitterBeetles (such as Darkling, Hide, and Carrion), Mosquitoes, Pillbugs,Scorpions, Spiders, Spider Mites (Twospotted, Spruce), Ticks.

The compounds of the invention may be used to control ornamental pestsincluding: Ants (Including Imported fire ants), Armyworms, Azaleacaterpillars, Aphids, Bagworms, Black vine weevils (adult), Boxelderbugs, Budworms, California oakworms, Cankerworms, Cockroaches, Crickets,Cutworms, Eastern tent caterpillars, Elm leaf beetles, Europeansawflies, Fall webworms, Flea beetles, Forest tent caterpillars, Gypsymoth larvae, Japanese beetles (adults), June beetles (adults), Lacebugs, Leaf-feeding caterpillars, Leafhoppers, Leafminers (adults), Leafrollers, Leaf skeletonizers, Midges, Mosquitoes, Oleander moth larvae,Pillbugs, Pine sawflies, Pine shoot beetles, Pinetip moths, Plant bugs,Root weevils, Sawflies, Scale insects (crawlers), Spiders, Spittlebugs,Striped beetles, Striped oakworms, Thrips, Tip moths, Tussock mothlarvae, Wasps, Broadmites, Brown softscales, California redscales(crawlers), Clover mites, Mealybugs, Pineneedlescales (crawlers), Spidermites, Whiteflies

The compounds of the invention may be used to control turf pestsincluding: Ants (Including Imported fire ants, Armyworms, Centipedes,Crickets, Cutworms, Earwigs, Fleas (adult), Grasshoppers, Japanesebeetles (adult), Millipedes, Mites, Mosquitoes (adult), Pillbugs, Sodwebworms, Sow bugs, Ticks (including species which transmit Lymedisease), Bluegrass billbugs (adult), Black turfgrass ataenius (adult),Chiggers, Fleas (adult), Grubs (suppression), Hyperodes weevils (adult),Mole crickets (nymphs and young adults), Mole Crickets (mature adults),Chinch Bugs.

The compounds of formula (I) and mixture of the invention, in particularthose in the tables above, may be used for soil applications, includingas a seed application, to target at least the following: sucking pestssuch as aphids, thrips, brown plant hopper (e.g. on rice), sting bugs,white flies (e.g. on cotton and vegetables), mites; on soil pests suchas corn root worm, wireworms, white grubs, zabrus, termites (e.g. onsugar cane, soy, pasture), maggots, cabbage root fly, red legged earthmite; on lepidoptera, such as spodoptera, cutworms, elasmoplpus,plutella (e.g. brassica), stem borers, leaf miners, flea beetle,Sternechus; on nematicides, such as Heterodera glycines (e.g. onsoybean), Pratylenchus brachyurus (e.g. on corn), P. zeae (e.g. oncorn),P. penetrans (e.g. on corn), Meloidogyne incognita (e.g. on vegetables),Heterodera schachtii (e.g. on sugar beet), Rotylenchus reniformis (e.g.on cotton), Heterodera avenae (e.g. on cereals), Pratylenchus neglectus(e.g. on cereals), thornei (e.g. on cereals).

The compounds of formula (I) and mixture of the invention, in particularthose in the tables above may be used for seed applications at least onthe following: soil grubs for corn, soybeans, sugarcane: Migdolus spp;Phyllophaga spp.; Diloboderus spp; Cyclocephala spp; Lyogenys fuscus;sugarcane weevils: Sphenophorus levis & Metamasius hemtpterus; termitesfor soybeans, sugarcane, pasture, others: Heterotermes tenuis;Heterotermes longiceps; Cornitermes cumulans; Procornitermes triacifer;Neocapritermes opacus; Neocapritermes parvus; corn root worms for cornand potatoes: Diabrotica spp., seed Maggot: Delia platura; soilstinkbugs: Scaptocoris castanea; wireworms: Agriotes spp; Athous sppHipnodes bicolor; Ctenicera destructor; Limonius canu; Limoniuscalifornicus; rice water weevil: Lissorhoptrus oryzophilus; Red Leggedearth mites: Halotydeus destructor.

The invention therefore provides a method of combating and/orcontrolling an animal pest, e.g. an invertebrate animal pest, whichcomprises applying to the pest, to a locus of the pest, or to a plantsusceptible to attack by the pest a pesticidally effective amount of acompound of formula (I). In particular, the invention provides a methodof combating and/or controlling insects, acarines, nematodes or molluscswhich comprises applying an insecticidally, acaricidally, nematicidallyor molluscicidally effective amount of a compound of formula (I), or acomposition containing a compound of formula (I), to a pest, a locus ofpest, preferably a plant, or to a plant susceptible to attack by a pest,The compounds of formula (I) are preferably used against insects,acarines or nematodes.

The term “plant” as used herein includes seedlings, bushes and trees.Crops are to be understood as also including those crops which have beenrendered tolerant to herbicides or classes of herbicides (e.g. ALS—,GS—, EPSPS—, PPO- and HPPD-inhibitors) by conventional methods ofbreeding or by genetic engineering. An example of a crop that has beenrendered tolerant to imidazolinones, e.g. imazamox, by conventionalmethods of breeding is Clearfield® summer rape (canola). Examples ofcrops that have been rendered tolerant to herbicides by geneticengineering methods include e.g. glyphosate- and glufosinate-resistantmaize varieties commercially available under the trade namesRoundupReady® and LibertyLink®.

The compounds of the invention may be applied to plant parts. Plantparts are to be understood as meaning all parts and organs of plantsabove and below the ground, such as shoot, leaf, flower and root,examples which may be mentioned being leaves, needles, stalks, stems,flowers, fruit bodies, fruits, seeds, roots, tubers and rhizomes. Theplant parts also include harvested material, and vegetative andgenerative propagation material, for example cuttings, tubers, rhizomes,offshoots and seeds. Treatment according to the invention of the plantsand plant parts with the active compounds is carried out directly or byallowing the compounds to act on their surroundings, habitat or storagespace by the customary treatment methods, for example by immersion,spraying, evaporation, fogging, scattering, painting on, injecting and,in the case of propagation material, in particular in the case of seed,also by applying one or more coats.

Compounds of formula I may be used on transgenic plants (includingcultivars) obtained by genetic engineering methods and/or byconventional methods. These are understood as meaning plants havingnovel properties (“traits”) which have been obtained by conventionalbreeding, by mutagenesis or by recombinant DNA techniques. Depending onthe plant species or plant cultivars, their location and growthconditions (soils, climate, vegetation period, diet), the treatmentaccording to the invention may also result in superadditive“synergistic”) effects.

Thus, for example, reduced application rates and/or a widening of theactivity spectrum and/or an increase in the activity of the substancesand compositions which can be used according to the invention, betterplant growth, increased tolerance to high or low temperatures, increasedtolerance to drought or to water or soil salt content, increasedflowering performance, easier harvesting, accelerated maturation, higherharvest yields, higher quality and/or a higher nutritional value of theharvested products, better storage stability and/or processability ofthe harvested products are possible, which exceed the effects which wereactually to be expected.

The preferred transgenic plants or plant cultivars which are to betreated according to the invention include all plants which, by virtueof the genetic modification, received genetic material which impartsparticularly advantageous, useful traits to these plants. Examples ofsuch traits are better plant growth, increased tolerance to high or lowtemperatures, increased tolerance to drought or to water or soil saltcontent, increased flowering performance, easier harvesting, acceleratedmaturation, higher harvest yields, higher quality and/or a highernutritional value of the harvested products, better storage stabilityand/or processability of the harvested products.

Further and particularly emphasized examples of such traits are a betterdefence of the plants against animal and microbial pests, such asagainst insects, mites, phytopathogenic fungi, bacteria and/or viruses,and also increased tolerance of the plants to certain herbicidallyactive compounds.

Examples of transgenic plants which may be mentioned are the importantcrop plants, such as cereals (wheat, rice), maize, soybean, potatoes,sugar beet, tomatoes, peas and other vegetable varieties, cotton,tobacco, oilseed rape and also fruit plants (with the fruits apples,pears, citrus fruits and grapes).

Compounds of formula I may be used on transgenic plants that are capableof producing one or more pesticidal proteins which confer upon thetransgenic plant tolerance or resistance to harmful pests, e.g. insectpests, nematode pests and the like. Such pesticidal proteins include,without limitation, Cry proteins from Bacillus thuringiensis Cry1Ab,Cry1Ac, Cry1F, Cry2Ab, Cry2Ae, Cry3A, Cry3Bb, or Cry9C; engineeredproteins such as modified Cry3A (U.S. Pat. No. 7,030,295) or Cry1A.105;or vegetative insecticidal proteins such as Vip1, Vip2 or Vip3. A fulllist of Bt Cry proteins and VIPs useful in the invention can be found onthe worldwide web at Bacillus thuringiensis Toxin Nomenclature Databasemaintained by the University of Sussex (see also, Crickmore et al.(1998) Microbiol. Mol. Biol. Rev. 62:807-813). Other pesticidal proteinsuseful in the invention include proteins of bacteria colonizingnematodes, e.g. Photorhabdus spp. or Xenorhabdus spp.; toxins producedby animals, such as scorpion toxins, arachnid toxins, wasp toxins, orother insect-specific neurotoxins; toxins produced by fungi, suchStreptomycetes toxins, plant lectins, such as pea or barley lectins;agglutinins; proteinase inhibitors, such as trypsin inhibitors, serineprotease inhibitors, patatin, cystatin or papain inhibitors;ribosome-inactivating proteins (RIP), such as ricin, maize-RIP, abrin,luffin, saporin or bryodin; steroid metabolism enzymes, such as3-hydroxysteroid oxidase, ecdysteroid-IDP-glycosyl-transferase,cholesterol oxidases, ecdysone inhibitors or HMG-CoA-reductase; ionchannel blockers, such as blockers of sodium or calcium channels;juvenile hormone esterase; diuretic hormone receptors (helicokininreceptors); stilben synthase, bibenzyl synthase, chitinases orglucanases. Further examples of such pesticidal proteins or transgenicplants capable of synthesizing such proteins are disclosed, e.g., inEP-A 374753, WO 93/007278, WO 95/34656, EP-A 427529, EP-A 451878, WO03/18810 and WO 03/52073. The methods for producing such transgenicplants are generally known to the person skilled in the art and some ofwhich are commercially available such as Agrisure®CB (corn producingCry1Ab), Agrisure®RW (corn producing mCry3A), Agrisure® Viptera (cornhybrids producing Vip3Aa); Agrisure300GT (corn hybrids producing Cry1Aband mCry3A); YieldGard® (corn hybrids producing the Cry1Ab protein),YieldGard® Plus (corn hybrids producing Cry1Ab and Cry3Bb1), Genuity®SmartStax® (corn hybrids with Cry1A.105, Cry2Ab2, Cry1F, Cry34/35,Cry3Bb); Herculex® I (corn hybrids producing Cry1Fa) and Herculex®RW(corn hybrids producing Cry34Ab1, Cry35Ab1 and the enzymePhosphinothricin-N-Acetyltransferase [PAT]); NuCOTN®33B (cottoncultivars producing Cry1Ac), Bollgard®I (cotton cultivars producingCry1Ac), Bollgard®II (cotton cultivars producing Cry1Ac and Cry2Ab2) andVIPCOT® (cotton cultivars producing a Vip3Aa). Soybean Cyst Nematoderesistance soybean (SCN®−Syngenta) and soybean with Aphid resistanttrait (AMT®) are also of interest.

Further examples of such transgenic crops are:

1. Btll Maize from Syngenta Seeds SAS, Chemin de l′Hobit 27, F-31 790St. Sauveur, France, registration number C/FR/96/05/10. Geneticallymodified Zea mays which has been rendered resistant to attack by theEuropean corn borer (Ostrinia nubilalis and Sesamia nonagrioides) bytransgenic expression of a truncated CryIA(b) toxin. Bt11 maize alsotransgenically expresses the enzyme PAT to achieve tolerance to theherbicide glufosinate ammonium.

2. Bt176 Maize from Syngenta Seeds SAS, Chemin de l′Hobit 27, F-31 790St. Sauveur, France, registration number C/FR/96/05/10. Geneticallymodified Zea mays which has been rendered resistant to attack by theEuropean corn borer (Ostrinia nubilalis and Sesamia nonagrioides) bytransgenic expression of a CryIA(b) toxin. Bt176 maize alsotransgenically expresses the enzyme PAT to achieve tolerance to theherbicide glufosinate ammonium.

3. MIR604 Maize from Syngenta Seeds SAS, Chemin de l′Hobit 27, F-31 790St. Sauveur, France, registration number C/FR/96/05/10. Maize which hasbeen rendered insect-resistant by transgenic expression of a modifiedCryIIIA toxin. This toxin is Cry3A055 modified by insertion of acathepsin-D-protease recognition sequence. The preparation of suchtransgenic maize plants is described in WO 03/018810.

4. MON 863 Maize from Monsanto Europe S.A. 270-272 Avenue de Tervuren,B-1150 Brussels, Belgium, registration number C/DE/02/9. MON 863expresses a CryIIIB(b1) toxin and has resistance to certain Coleopterainsects.

5. IPC 531 Cotton from Monsanto Europe S.A. 270-272 Avenue de Tervuren,B-1150 Brussels, Belgium, registration number C/ES/96/02.

6. 1507 Maize from Pioneer Overseas Corporation, Avenue Tedesco, 7B-1160 Brussels, Belgium, registration number C/NL/00/10. Geneticallymodified maize for the expression of the protein Cry1F for achievingresistance to certain Lepidoptera insects and of the PAT protein forachieving tolerance to the herbicide glufosinate ammonium.

7. NK603 x MON 810 Maize from Monsanto Europe S.A. 270-272 Avenue deTervuren, B-1150 Brussels, Belgium, registration number C/GB/02/M3/03.Consists of conventionally bred hybrid maize varieties by crossing thegenetically modified varieties NK603 and MON 810. NK603 8 MON 810 Maizetransgenically expresses the protein CP4 EPSPS, obtained fromAgrobacterium sp. strain CP4, which imparts tolerance to the herbicideRoundup® (contains glyphosate), and also a CryIA(b) toxin obtained fromBacillus thuringiensis subsp. kurstaki which brings about tolerance tocertain Lepidoptera, include the European corn borer.

Further examples of transgenic plants, and of very high interest, arethose carrying traits conferring resistance to 2.4D (e.g. Enlist®) (e.g.WO 2011066384), glyphosate (e.g. Roundup Ready®, Roundup Ready 2Yield®), sulfonylurea (e.g. STS®), glufosinate (e.g. Liberty Link®,Ignite®), Dicamba (Monsanto), HPPD tolerance (e.g. isoxaflutoleherbicide) (Bayer CropScience, Syngenta). Double or triple stacks of anyof the traits described here are also of interest, including glyphosateand sulfonyl-urea tolerance ((e.g. Optimum GAT®), plants stacked withSTS® and Roundup Ready® or plants stacked with STS® and Roundup Ready 2Yield®), dicamba and glyphosate tolerance (Monsanto). Of particularinterest are soybean plants carrying trains conferring resistance to2.4D (e.g. Enlist®), glyphosate (e.g. Roundup Ready®, Roundup Ready 2Yield®), sulfonylurea (e.g. STS®), glufosinate (e.g. Liberty Link®,Ignite®), Dicamba (Monsanto) HPPD tolerance (e.g. isoxaflutoleherbicide) (Bayer CropScience, Syngenta). Double or triple stack insoybean plants of any of the traits described here are also of interest,including glyphosate and sulfonyl-urea tolerance (e.g. Optimum GAT®,plants stacked with STS® and Roundup Ready® or Roundup Ready 2 Yield®),dicamba and glyphosate tolerance (Monsanto).

Transgenic crops of insect-resistant plants are also described in BATS(Zentrum für Biosicherheit and Nachhaltigkeit, Zentrum BATS,Clarastrasse 13, 4058 Basel, Switzerland) Report 2003, (http://bats.ch).

Examples of cotton transgenic events include MON 531/757/1076 (BollgardI®−Monsanto), MON1445 (Roundup ready cotton®−Monsanto), MON531×MON1445(Bollgard I+RR®−Monsanto), MON15985 (Genuity Bollgard IIcotton®−Monsanto), MON88913 (Genuity RR FLEX cotton®−Monsanto),MON15985×MON1445 (Genuity Bollgard II+RR FELX cotton®−Monsanto),MON15983×MON88913 (Genuity Bollgard II+RR FLEX cotton®−Monsanto),MON15985 (FibreMax Bollgard II Cotton®−Monsanto), LL25 (FibreMax LLcotton®−BCS Stoneville), GHB614 (FibreMax GlyTol cotton®−BCSStoneville), LL25×MON15985 (FibreMax LL Bollgard II cotton®−BCSStoneville/Monsanto), GHB614×LL25 (FibreMax LL GlyTol cotton®−BCSStoneville), GHB614×LL25×MON15985 (FibreMax RR GlyTol Bollgard IIcotton®−BCS Stoneville), MON88913×MON15985 (FibreMax LL GlyTol BollgardII cotton®−Monsanto), MON88913 (FibreMax RR Flex cotton®−Monsanto),GHB119+T304-40 (Twinlink®−BCS Stoneville), GHB119+T304-40×LL25×GHB614(Twinlink LL GT®−BCS Stoneville), 3006-210-23×281-24-236 (PhytoGenWidestrike Insect Protection®−Dow), 3006-210-23×281-24-236×MON88913(PhytoGen Widestrike Insect Protection+RR FLEX−® Dow/Monsanto),3006-210-23×281-24-236×MON1445 ((PhytoGen Widestrike InsectProtection+RR®−Dow/Monsanto), MON1445 (PhytoGen RoundupReady®−Monsanto), MON88913 (PhytoGen Roundup Ready FLEX®−Monsanto),COT102×COT67B (Vipcot®−Syngenta), COT102×COT67B×MON88913 (Vipcot RRFLEX®−Syngenta/Monsanto), 281-24-236 (Dow), 3006-210-23 (Dow), COT102(Syngenta), COT67B (Syngenta), T304-40 (BCS Stoneville).

Examples of Soy transgenic events include MON87701×MON89788 (GenuityRoundup ready 2 Yield soybeans®−Monsanto), MON89788 (RoundupReady2Yield®, RR2Y®−Monsanto), MON87708 (Monsanto), 40-3-2 (RoundupReady®, RR1®−Monsanto), MON87701 (Monsanto), DAS-68416 (Enlist WeedControl System®−Dow), DP356043 (Optimum GAT®−Pioneer), A5547-127(LibertyLink soybean®−Bayercropscience), A2704-12 (Bayercropscience),GU262 (Bayercropscience), W62 W98 (Bayercropscience), CRV127(Cultivance®−BASF/EMBRAPA) SYHT0H2 (WO2012/082548).

Examples of Maize transgenic events include T25 (LibertyLink®,LL®−Bayerscropscience), DHT-1 (Dow), TC1507 (Herculex I®−Dow),DAS59122-7 (Herculex RW®−Dow), TC1507+DAS59122-7−Herculex Xtra®−Dow),TC1507×DAS-59122-7×NK603 (Herculex Xtra+RR®−Dow),TC1507×DAS-59122-×MON88017×MON89034 (Genuity Smartstax corn®, GenuitySmartstax RIB complete®−Monsanto/Dow), MON89034×NK603 (Genuity VT doublePRO®−Monsanto), MON89034+MON88017 (Genuity VT Triple PRO®−Monsanto),NK603 (Roundup Ready2®, RR2®−Monsanto), MON810 (YieldGard BT®, Yieldgardcornborer®−Monsanto), MON810×NK603 (YieldGard cornborer RR Corn200−Monasnto), MON810×MON863 (YieldGard Plus®−Monsanto),MON863×MON810×NK603 (YieldGard Plus+RR Corn2®/YieldGard RRMaize®−Monsanto), MON863×NK603 (YieldGard Rotworm+RR Corn 2®−Monsanto),MON863 (YieldBard RW®−Monsanto), MON89034 (YieldGard RW®−Monsanto),MON88017 (YieldGard VT RW®−Monsanto), MON810+MON88017 (YieldGard VTTriple®−Monsanto), MON88017+MON89034 (YieldGard VT TriplePro®−Monsanto), Bt11+MIR604+GA21 (Agrisure 3000®−Syngenta), Btl1+TC1507+MIR604+5307+GA21 (Syngenta), Bt11+TC1507+MIR604+DAS59122+GA21(Agrisure 3122®−Syngenta), BT11 (Agrisure CB®−Syngenta), GA21−(AgrisureGT®−Syngenta), MIR604 (Agrisure RW®−Syngenta), Bt11+MIR162 (Agrisure TLVIP®−Syngenta), BT11+MIR162+GA21 (Agrisure Viptra 3110®−Syngenta),BT11+MIR162+MIR604 (Agrisure TM 3100®−Syngenta),Event3272+BT11+MIR604+GA21 (Syngenta), BT11+MIR1692+MIR604+GA21(Agrisure Viptera 3111®−Syngenta), BT11+MIR 162+TC1507+GA21 (AgrisureViptera 3220®−Syngenta), BT11+MIR162+TC1507+MIR604+5307+GA21 (AgrisureViptera 3222®−Syngenta), MIR162 (Syngenta), BT11+GA21+MIR162+MIR604+5307(Syngenta), 5307 (Syngenta).

In order to apply a compound of formula (I) as an insecticide,acaricide, nematicide or molluscicide to a pest, a locus of pest, or toa plant susceptible to attack by a pest, a compound of formula (I) isusually formulated into a composition which includes, in addition to thecompound of formula (I), a suitable inert diluent or carrier and,optionally, a surface active agent (SFA). SFAs are chemicals which areable to modify the properties of an interface (for example,liquid/solid, liquid/air or liquid/liquid interfaces) by lowering theinterfacial tension and thereby leading to changes in other properties(for example dispersion, emulsification and wetting). It is preferredthat all compositions (both solid and liquid formulations) comprise, byweight, 0.0001 to 95%, more preferably 1 to 85%, for example 5 to 60%,of a compound of formula (I). The composition is generally used for thecontrol of pests such that a compound of formula (I) is applied at arate of from 0.1 g to 10 kg per hectare, preferably from 1 g to 6 kg perhectare, more preferably from lg to lkg per hectare.

When used in a seed dressing, a compound of formula (I) is generallyused at a rate of 0.0001 g to 10 g (for example 0.001 g or 0.05 g),preferably 0.005 g to 10 g, more preferably 0.005 g to 4 g, per kilogramof seed.

In another aspect the present invention provides a compositioncomprising a pesticidally effective amount of a compound of formula (I),in particular an insecticidal, acaricidal, nematicidal or molluscicidalcomposition comprising an insecticidally, acaricidally, nematicidally ormolluscicidally effective amount of a compound of formula (I) and asuitable carrier or diluent therefor. The composition is preferably aninsecticidal, acaricidal, nematicidal or molluscicidal composition.

The compositions can be chosen from a number of formulation types,including dustable powders (DP), soluble powders (SP), water solublegranules (SG), water dispersible granules (WG), wettable powders (WP),granules (GR) (slow or fast release), soluble concentrates (SL), oilmiscible liquids (OL), ultra low volume liquids (UL), emulsifiableconcentrates (EC), dispersible concentrates (DC), emulsions (both oil inwater (EW) and water in oil (EO)), micro-emulsions (ME), suspensionconcentrates (SC), aerosols, fogging/smoke formulations, capsulesuspensions (CS) and seed treatment formulations. The formulation typechosen in any instance will depend upon the particular purpose envisagedand the physical, chemical and biological properties of the compound offormula (I).

Dustable powders (DP) may be prepared by mixing a compound of formula(I) with one or more solid diluents (for example natural clays, kaolin,pyrophyllite, bentonite, alumina, montmorillonite, kieselguhr, chalk,diatomaceous earths, calcium phosphates, calcium and magnesiumcarbonates, sulfur, lime, flours, talc and other organic and inorganicsolid carriers) and mechanically grinding the mixture to a fine powder.

Soluble powders (SP) may be prepared by mixing a compound of formula (I)with one or more water-soluble inorganic salts (such as sodiumbicarbonate, sodium carbonate or magnesium sulfate) or one or morewater-soluble organic solids (such as a polysaccharide) and, optionally,one or more wetting agents, one or more dispersing agents or a mixtureof said agents to improve water dispersibility/solubility. The mixtureis then ground to a fine powder Similar compositions may also begranulated to form water soluble granules (SG).

Wettable powders (WP) may be prepared by mixing a compound of formula(I) with one or more solid diluents or carriers, one or more wettingagents and, preferably, one or more dispersing agents and, optionally,one or more suspending agents to facilitate the dispersion in liquids.The mixture is then ground to a fine powder. Similar compositions mayalso be granulated to form water dispersible granules (WG).

Granules (GR) may be formed either by granulating a mixture of acompound of formula (I) and one or more powdered solid diluents orcarriers, or from pre-formed blank granules by absorbing a compound offormula (I) (or a solution thereof, in a suitable agent) in a porousgranular material (such as pumice, attapulgite clays, fuller's earth,kieselguhr, diatomaceous earths or ground corn cobs) or by adsorbing acompound of formula (I) (or a solution thereof, in a suitable agent) onto a hard core material (such as sands, silicates, mineral carbonates,sulfates or phosphates) and drying if necessary. Agents which arecommonly used to aid absorption or adsorption include solvents (such asaliphatic and aromatic petroleum solvents, alcohols, ethers, ketones andesters) and sticking agents (such as polyvinyl acetates, polyvinylalcohols, dextrins, sugars and vegetable oils). One or more otheradditives may also be included in granules (for example an emulsifyingagent, wetting agent or dispersing agent).

Dispersible Concentrates (DC) may be prepared by dissolving a compoundof formula (I) in water or an organic solvent, such as a ketone, alcoholor glycol ether. These solutions may contain a surface active agent (forexample to improve water dilution or prevent crystallization in a spraytank).

Emulsifiable concentrates (EC) or oil-in-water emulsions (EW) may beprepared by dissolving a compound of formula (I) in an organic solvent(optionally containing one or more wetting agents, one or moreemulsifying agents or a mixture of said agents). Suitable organicsolvents for use in ECs include aromatic hydrocarbons (such asalkylbenzenes or alkylnaphthalenes, exemplified by SOLVESSO 100,SOLVESSO 150 and SOLVESSO 200; SOLVESSO is a Registered Trade Mark),ketones (such as cyclohexanone or methylcyclohexanone) and alcohols(such as benzyl alcohol, furfuryl alcohol or butanol),N-alkylpyrrolidones (such as N-methylpyrrolidone or N-octylpyrrolidone),dimethyl amides of fatty acids (such as C₈-C₁₀ fatty acid dimethylamide)and chlorinated hydrocarbons. An EC product may spontaneously emulsifyon addition to water, to produce an emulsion with sufficient stabilityto allow spray application through appropriate equipment. Preparation ofan EW involves obtaining a compound of formula (I) either as a liquid(if it is not a liquid at room temperature, it may be melted at areasonable temperature, typically below 70° C.) or in solution (bydissolving it in an appropriate solvent) and then emulsifiying theresultant liquid or solution into water containing one or more SFAs,under high shear, to produce an emulsion. Suitable solvents for use inEWs include vegetable oils, chlorinated hydrocarbons (such aschlorobenzenes), aromatic solvents (such as alkylbenzenes oralkylnaphthalenes) and other appropriate organic solvents which have alow solubility in water.

Microemulsions (ME) may be prepared by mixing water with a blend of oneor more solvents with one or more SFAs, to produce spontaneously athermodynamically stable isotropic liquid formulation. A compound offormula (I) is present initially in either the water or the solvent/SFAblend. Suitable solvents for use in MEs include those hereinbeforedescribed for use in ECs or in EWs. An ME may be either an oil-in-wateror a water-in-oil system (which system is present may be determined byconductivity measurements) and may be suitable for mixing water-solubleand oil-soluble pesticides in the same formulation. An ME is suitablefor dilution into water, either remaining as a microemulsion or forminga conventional oil-in-water emulsion.

Suspension concentrates (SC) may comprise aqueous or non-aqueoussuspensions of finely divided insoluble solid particles of a compound offormula (I). SCs may be prepared by ball or bead milling the solidcompound of formula (I) in a suitable medium, optionally with one ormore dispersing agents, to produce a fine particle suspension of thecompound. One or more wetting agents may be included in the compositionand a suspending agent may be included to reduce the rate at which theparticles settle. Alternatively, a compound of formula (I) may be drymilled and added to water, containing agents hereinbefore described, toproduce the desired end product.

Aerosol formulations comprise a compound of formula (I) and a suitablepropellant (for example n-butane). A compound of formula (I) may also bedissolved or dispersed in a suitable medium (for example water or awater miscible liquid, such as n-propanol) to provide compositions foruse in non-pressurized, hand-actuated spray pumps.

A compound of formula (I) may be mixed in the dry state with apyrotechnic mixture to form a composition suitable for generating, in anenclosed space, a smoke containing the compound.

Capsule suspensions (CS) may be prepared in a manner similar to thepreparation of EW formulations but with an additional polymerizationstage such that an aqueous dispersion of oil droplets is obtained, inwhich each oil droplet is encapsulated by a polymeric shell and containsa compound of formula (I) and, optionally, a carrier or diluenttherefor. The polymeric shell may be produced by either an interfacialpolycondensation reaction or by a coacervation procedure. Thecompositions may provide for controlled release of the compound offormula (I) and they may be used for seed treatment. A compound offormula (I) may also be formulated in a biodegradable polymeric matrixto provide a slow, controlled release of the compound.

A composition may include one or more additives to improve thebiological performance of the composition (for example by improvingwetting, retention or distribution on surfaces; resistance to rain ontreated surfaces; or uptake or mobility of a compound of formula (I)).Such additives include surface active agents, spray additives based onoils, for example certain mineral oils or natural plant oils (such assoy bean and rape seed oil), and blends of these with otherbio-enhancing adjuvants (ingredients which may aid or modify the actionof a compound of formula (I)).

A compound of formula (I) may also be formulated for use as a seedtreatment, for example as a powder composition, including a powder fordry seed treatment (DS), a water soluble powder (SS) or a waterdispersible powder for slurry treatment (WS), or as a liquidcomposition, including a flowable concentrate (FS), a solution (LS) or acapsule suspension (CS). The preparations of DS, SS, WS, FS and LScompositions are very similar to those of, respectively, DP, SP, WP, SCand DC compositions described above. Compositions for treating seed mayinclude an agent for assisting the adhesion of the composition to theseed (for example a mineral oil or a film-forming barrier).

Wetting agents, dispersing agents and emulsifying agents may be surfaceSFAs of the cationic, anionic, amphoteric or non-ionic type.

Suitable SFAs of the cationic type include quaternary ammonium compounds(for example cetyltrimethyl ammonium bromide), imidazolines and aminesalts.

Suitable anionic SFAs include alkali metals salts of fatty acids, saltsof aliphatic monoesters of sulfuric acid (for example sodium laurylsulfate), salts of sulfonated aromatic compounds (for example sodiumdodecylbenzenesulfonate, calcium dodecylbenzenesulfonate,butylnaphthalene sulfonate and mixtures of sodium di-isopropyl- andtri-isopropyl-naphthalene sulfonates), ether sulfates, alcohol ethersulfates (for example sodium laureth-3-sulfate), ether carboxylates (forexample sodium laureth-3-carboxylate), phosphate esters (products fromthe reaction between one or more fatty alcohols and phosphoric acid(predominately mono-esters) or phosphorus pentoxide (predominatelydi-esters), for example the reaction between lauryl alcohol andtetraphosphoric acid; additionally these products may be ethoxylated),sulfosuccinamates, paraffin or olefine sulfonates, taurates andlignosulfonates.

Suitable SFAs of the amphoteric type include betaines, propionates andglycinates.

Suitable SFAs of the non-ionic type include condensation products ofalkylene oxides, such as ethylene oxide, propylene oxide, butylene oxideor mixtures thereof, with fatty alcohols (such as oleyl alcohol or cetylalcohol) or with alkylphenols (such as octylphenol, nonylphenol oroctylcresol); partial esters derived from long chain fatty acids orhexitol anhydrides; condensation products of said partial esters withethylene oxide; block polymers (comprising ethylene oxide and propyleneoxide); alkanolamides; simple esters (for example fatty acidpolyethylene glycol esters); amine oxides (for example lauryl dimethylamine oxide); and lecithins.

Suitable suspending agents include hydrophilic colloids (such aspolysaccharides, polyvinylpyrrolidone or sodium carboxymethylcellulose)and swelling clays (such as bentonite or attapulgite).

A compound of formula (I) may be applied by any of the known means ofapplying pesticidal compounds. For example, it may be applied,formulated or unformulated, to the pests or to a locus of the pests(such as a habitat of the pests, or a growing plant liable toinfestation by the pests) or to any part of the plant, including thefoliage, stems, branches or roots, to the seed before it is planted orto other media in which plants are growing or are to be planted (such assoil surrounding the roots, the soil generally, paddy water orhydroponic culture systems), directly or it may be sprayed on, dustedon, applied by dipping, applied as a cream or paste formulation, appliedas a vapor or applied through distribution or incorporation of acomposition (such as a granular composition or a composition packed in awater-soluble bag) in soil or an aqueous environment.

A compound of formula (I) may also be injected into plants or sprayedonto vegetation using electrodynamic spraying techniques or other lowvolume methods, or applied by land or aerial irrigation systems.

Compositions for use as aqueous preparations (aqueous solutions ordispersions) are generally supplied in the form of a concentratecontaining a high proportion of the active ingredient, the concentratebeing added to water before use. These concentrates, which may includeDCs, SCs, ECs, EWs, MEs, SGs, SPs, WPs, WGs and CSs, are often requiredto withstand storage for prolonged periods and, after such storage, tobe capable of addition to water to form aqueous preparations whichremain homogeneous for a sufficient time to enable them to be applied byconventional spray equipment. Such aqueous preparations may containvarying amounts of a compound of formula (I) (for example 0.0001 to 10%,by weight) depending upon the purpose for which they are to be used.

A compound of formula (I) may be used in mixtures with fertilizers (forexample nitrogen-, potassium- or phosphorus-containing fertilizers).Suitable formulation types include granules of fertilizer. The mixturespreferably contain up to 25% by weight of the compound of formula (I).

The invention therefore also provides a fertilizer compositioncomprising a fertilizer and a compound of formula (I).

The compositions of this invention may contain other compounds havingbiological activity, for example micronutrients or compounds havingfungicidal activity or which possess plant growth regulating,herbicidal, insecticidal, nematicidal or acaricidal activity.

The compound of formula (I) may be the sole active ingredient of thecomposition or it may be admixed with one or more additional activeingredients such as a pesticide, e.g. a insecticide, fungicide orherbicide, or a synergist or plant growth regulator where appropriate.An additional active ingredient may provide a composition having abroader spectrum of activity or increased persistence at a locus;synergize the activity or complement the activity (for example byincreasing the speed of effect or overcoming repellency) of the compoundof formula (I); or help to overcome or prevent the development ofresistance to individual components. The particular additional activeingredient will depend upon the intended utility of the composition.

Examples of suitable pesticides include the following

-   a) Pyrethroids, such as permethrin, cypermethrin, fenvalerate,    esfenvalerate, deltamethrin, cyhalothrin (in particular    lambda-cyhalothrin and gamma cyhalothrin), bifenthrin,    fenpropathrin, cyfluthrin, tefluthrin, fish safe pyrethroids (for    example ethofenprox), natural pyrethrin, tetramethrin,    S-bioallethrin, fenfluthrin, prallethrin, acrinathirin, etofenprox    or    5-benzyl-3-furylmethyl-(E)-(1R,3S)-2,2-dimethyl-3-(2-oxothiolan-3-ylidenemethyl)cyclopropane    carboxylate;-   b) Organophosphates, such as profenofos, sulprofos, acephate, methyl    parathion, azinphos-methyl, demeton-s-methy 1, heptenophos,    thiometon, fenamiphos, monocrotophos, profenofos, triazophos,    methamidophos, dimethoate, phosphamidon, malathion, chlorpyrifos,    phosalone, terbufos, fensulfothion, fonofos, phorate, phoxim,    pirimiphos-methyl, pirimiphos-ethyl, fenitrothion, fosthiazate or    diazinon;-   c) Carbamates (including aryl carbamates), such as pirimicarb,    triazamate, cloethocarb, carbofuran, furathiocarb, ethiofencarb,    aldicarb, thiofurox, carbosulfan, bendiocarb, fenobucarb, propoxur,    methomyl or oxamyl;-   d) Benzoyl ureas, such as diflubenzuron, triflumuron, hexaflumuron,    flufenoxuron, diafenthiuron, lufeneron, novaluron, noviflumuron or    chlorfluazuron;-   e) Organic tin compounds, such as cyhexatin, fenbutatin oxide or    azocyclotin;-   f) Pyrazoles, such as tebufenpyrad, tolfenpyrad, ethiprole,    pyriprole, fipronil, and fenpyroximate;-   g) Macrolides, such as avermectins or milbemycins, for example    abamectin, emamectin benzoate, ivermectin, milbemycin, spinosad,    azadirachtin, milbemectin, lepimectin or spinetoram;-   h) Hormones or pheromones;-   i) Organochlorine compounds, such as endosulfan (in particular    alpha-endosulfan), benzene hexachloride, DDT, chlordane or dieldrin;-   j) Amidines, such as chlordimeform or amitraz;-   k) Fumigant agents, such as chloropicrin, dichloropropane, methyl    bromide or metam;-   l) Neonicotinoid compounds, such as imidacloprid, thiacloprid,    acetamiprid, nitenpyram, dinotefuran, thiamethoxam, clothianidin, or    nithiazine;-   m) Diacylhydrazines, such as tebufenozide, chromafenozide or    methoxyfenozide;-   n) Diphenyl ethers, such as diofenolan or pyriproxifen;-   o) Pyrazolines such as Indoxacarb or metaflumizone;-   p) Ketoenols, such as Spirotetramat, spirodiclofen or spiromesifen;-   q) Diamides, such as flubendiamide, chlorantraniliprole (Rynaxypyr®)    or cyantraniliprole;-   r) Essential oils such as Bugoil®—(PlantImpact); or-   s) a comopund selected from buprofezine, flonicamid, acequinocy 1,    bifenazate, cyenopyrafen, cyflumetofen, etoxazole, flometoquin,    fluacrypyrim, fluensulfone, flufenerim, flupyradifuone, harpin,    iodomethane, dodecadienol, pyridaben, pyridalyl, pyrimidifen,    flupyradifurone,    4-[(6-Chloro-pyridin-3-ylmethyl)-(2,2-difluoro-ethyl)-amino]-5H-furan-2-one    (DE 102006015467), CAS: 915972-17-7 (WO 2006129714; WO2011/147953;    WO2011/147952), CAS: 26914-55-8 (WO 2007020986), chlorfenapyr,    pymetrozine, sulfoxaflor and pyrifluqinazon.

In addition to the major chemical classes of pesticide listed above,other pesticides having particular targets may be employed in thecomposition, if appropriate for the intended utility of the composition.For instance, selective insecticides for particular crops, for examplestemborer specific insecticide (combinations such as cartap) or hopperspecific insecticides (combinations such as buprofezin) for use in ricemay be employed. Alternatively insecticides or acaricides specific forparticular insect species/stages may also be included in thecompositions (for example acaricidal ovo-larvicides, to givecombinations such as clofentezine, flubenzimine, hexythiazox ortetradifon; acaricidal motilicides, to give combinations such as dicofolor propargite ; acaricides, to give combinations such as bromopropylateor chlorobenzilate ; or growth regulators, such as hydramethylnon,cyromazine, methoprene, chlorfluazuron or diflubenzuron).

Examples of fungicidal compounds and combinations which may be includedin the composition of the invention are(E)-N-methyl-2-[2-(2,5-dimethylphenoxymethyl)phenyl]-2-methoxy-iminoacetamide(SSF-129),4-bromo-2-cyano-N,N-dimethyl-6-trifluoromethylbenzimidazole-1-sulfonamide,α-[N-(3-chloro-2,6-xylyl)-2-methoxyacetamido]-γ-butyrolactone,4-chloro-2-cyano-N,N-dimethyl-5-p-tolylimidazole-1-sulfonamide (IKF-916,cyamidazosulfamid),3-5-dichloro-N-(3-chloro-1-ethyl-1-methyl-2-oxopropyl)-4-methylbenzamide(RH-7281, zoxamide),N-allyl-4,5,-dimethyl-2-trimethylsilylthiophene-3-carboxamide(MON65500),N-(1-cyano-1,2-dimethylpropyl)-2-(2,4-dichlorophenoxy)propionamide(AC382042), N-(2-methoxy-5-pyridyl)-cyclopropane carboxamide,acibenzolar (CGA245704) (e.g. acibenzolar-S-methyl), alanycarb,aldimorph, anilazine, azaconazole, azoxystrobin, benalaxyl, benomyl,benthiavalicarb, biloxazol, bitertanol, bixafen, blasticidin S,boscalid, bromuconazole, bupirimate, captafol, captan, carbendazim,carbendazim , chlorhydrate, carboxin, carpropamid, carvone, CGA41396,CGA41397, chinomethionate, chlorothalonil, chlorozolinate, clozylacon,copper containing compounds to give combintations such as copperoxychloride, copper oxyquinolate, copper sulfate, copper tallate andBordeaux mixture, cyclufenamid, cymoxanil, cyproconazole, cyprodinil,debacarb, di-2-pyridyl disulfide 1,1′-dioxide, dichlofluanid,diclomezine, dicloran, diethofencarb, difenoconazole, difenzoquat,diflumetorim, O,O-di-iso-propyl-S-benzyl thiophosphate, dimefluazole,dimetconazole, dimethomorph, dimethirimol, diniconazole, dinocap,dithianon, dodecyl dimethyl ammonium chloride, dodemorph, dodine,doguadine, edifenphos, epoxiconazole, ethirimo 1,ethyl-(Z)-N-benzyl-N-qmethyl([methyl-thioethylideneaminooxycarbonyl)amino]thio)-β-alaninate,etridiazole, famoxadone, fenamidone (RPA407213), fenarimol,fenbuconazole, fenfuram, fenhexamid (KBR2738), fenpiclonil, fenpropidin,fenpropimorph, fentin acetate, fentin hydroxide, ferbam, ferimzone,fluazinam, fludioxonil, flumetover, fluopyram, fluoxastrobin,fluoroimide, fluquinconazole, flusilazole, flutolanil, flutriafol,fluxapyroxad, folpet, fuberidazole, furalaxyl, furametpyr, guazatine,hexaconazole, hydroxyisoxazole, hymexazole, imazalil, imibenconazole,iminoctadine, iminoctadine triacetate, ipconazole, iprobenfos,iprodione, iprovalicarb (SZX0722), isopropanyl butyl carbamate,isoprothiolane, isopyrazam, kasugamycin, kresoxim-methyl, LY186054,LY211795, LY248908, mancozeb, mandipropamid, maneb, mefenoxam,metalaxyl, mepanipyrim, mepronil, metalaxyl, metconazole, metiram,metiram-zinc, metominostrobin, myclobutanil, neoasozin, nickeldimethyldithiocarbamate, nitrothal-isopropyl, nuarimol, ofurace,organomercury compounds, oxadixyl, oxasulfuron, oxolinic acid,oxpoconazole, oxycarboxin, pefurazoate, penconazole, pencycuron,penflufen, penthiopyrad, phenazin oxide, phosetyl-Al, phosphorus acids,phthalide, picoxystrobin (ZA1963), polyoxinD, polyram, probenazole,prochloraz, procymidone, propamocarb, propiconazole, propineb, propionicacid, prothioconazole, pyrazophos, pyrifenox, pyrimethanil,pyraclostrobin, pyroquilon, pyroxyfur, pyrrolnitrin, quaternary ammoniumcompounds, quinomethionate, quinoxyfen, quintozene, sedaxane,sipconazole (F-155), sodium pentachlorophenate, spiroxamine,streptomycin, sulfur, tebuconazole, tecloftalam, tecnazene,tetraconazole, thiabendazole, thifluzamid,2-(thiocyanomethylthio)benzothiazole, thiophanate-methyl, thiram,timibenconazole, tolclofos-methyl, tolylfluanid, triadimefon,triadimenol, triazbutil, triazoxide, tricyclazole, tridemorph,trifloxystrobin (CGA279202), triforine, triflumizole, triticonazole,validamycin A, vapam, vinclozolin, zineb and ziram,N-[9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide[1072957-71-1], 1-methyl-3-difluoromethyl-1H-pyrazole-4-carboxylic acid(2-dichloromethylene-3-ethyl-1-methyl-indan-4-yl)-amide, and1-methyl-3-difluoromethyl-4H-pyrazole-4-carboxylic acid[2-(2,4-dichloro-phenyl)-2-methoxy-1-methyl-ethyl]-amide.

The active ingredients combinations described above comprising acompound selected of the invention, in particulary from Tables 1 to 312and an active ingredient as described above are preferably combined in amixing ratio of from 100:1 to 1:6000, especially from 50:1 to 1:50, moreespecially in a ratio of from 20:1 to 1:20, even more especially from10:1 to 1:10, very especially from 5:1 and 1:5, special preference beinggiven to a ratio of from 2:1 to 1:2, and a ratio of from 4:1 to 2:1being likewise preferred, above all in a ratio of 1:1, or 5:1, or 5:2,or 5:3, or 5:4, or 4:1, or 4:2, or 4:3, or 3:1, or 3:2, or 2:1, or 1:5,or 2:5, or 3:5, or 4:5, or 1:4, or 2:4, or 3:4, or 1:3, or 2:3, or 1:2,or 1:600, or 1:300, or 1:150, or 1:35, or 2:35, or 4:35, or 1:75, or2:75, or 4:75, or 1:6000, or 1:3000, or 1:1500, or 1:350, or 2:350, or4:350, or 1:750, or 2:750, or 4:750. Those mixing ratios are understoodto include, on the one hand, ratios by weight and also, on other hand,molar ratios.

In addition, biological agents may be included in the composition of theinvention e.g. Baciullus species such as Bacillus firmus, Bacilluscereus, Bacillus subtilis, and Pasteuria species such as Pasteuriapenetrans and Pasteuria nishizawae. A suitable Bacillus firmus strain isstrain CNCM I-1582 which is commercially available as BioNem™. Asuitable Bacillus cereus strain is strain CNCM 1-1562. Of both Bacillusstrains more details can be found in U.S. Pat. No. 6,406,690. Otherbiological organisms that may be included in the compositions of theinvention are bacteria such as Streptomyces spp. such as S. avermitilis,and fungi such as Pochonia spp. such as P. chlamydosporia. Also ofinterest are Metarhizium spp. such as M. anisopliae; Pochonia spp. suchas P. chlamydosporia.

The compounds of formula (I) may be mixed with soil, peat or otherrooting media for the protection of plants against seed-borne,soil-borne or foliar fungal diseases.

Examples of suitable synergists for use in the compositions includepiperonyl butoxide, sesamex, safroxan and dodecyl imidazole.

Suitable herbicides and plant-growth regulators for inclusion in thecompositions will depend upon the intended target and the effectrequired.

An example of a rice selective herbicide which may be included ispropanil. An example of a plant growth regulator for use in cotton isPIX™.

Some mixtures may comprise active ingredients which have significantlydifferent physical, chemical or biological properties such that they donot easily lend themselves to the same conventional formulation type. Inthese circumstances other formulation types may be prepared. Forexample, where one active ingredient is a water insoluble solid and theother a water insoluble liquid, it may nevertheless be possible todisperse each active ingredient in the same continuous aqueous phase bydispersing the solid active ingredient as a suspension (using apreparation analogous to that of an SC) but dispersing the liquid activeingredient as an emulsion (using a preparation analogous to that of anEW). The resultant composition is a suspoemulsion (SE) formulation.

The compounds of the invention are also useful in the field of animalhealth, e.g. they may be used against parasitic invertebrate pests, morepreferably against parasitic invertebrate pests in or on an animal.Examples of pests include nematodes, trematodes, cestodes, flies, mites,tricks, lice, fleas, true bugs and maggots. The animal may be anon-human animal, e.g. an animal associated with agriculture, e.g. acow, a pig, a sheep, a goat, a horse, or a donkey, or a companionanimal, e.g. a dog or a cat.

In a further aspect the invention provides a compound of the inventionfor use in a method of therapeutic treatment.

In a further aspect the invention relates to a method of controllingparasitic invertebrate pests in or on an animal comprising administeringa pesticidally effective amount of a compound of the invention. Theadministration may be for example oral administration, parenteraladministration or external administration, e.g. to the surface of theanimal body. In a further aspect the invention relates to a compound ofthe invention for controlling parasitic invertebrate pests in or on ananimal. In a further aspect the invention relates to use of a compoundof the invention in the manufacture of a medicament for controllingparasitic invertebrate pests in or on an animal

In a further aspect, the invention relates to a method of controllingparasitic invertebrate pests comprising administering a pesticidallyeffective amount of a compound of the invention to the environment inwhich an animal resides.

In a further aspect the invention relates to a method of protecting ananimal from a parasitic invertebrate pest comprising administering tothe animal a pesticidally effective amount of a compound of theinvention. In a further aspect the invention relates to a compound ofthe invention for use in protecting an animal from a parasiticinvertebrate pest. In a further aspect the invention relates to use of acompound of the invention in the manufacture of a medicament forprotecting an animal from a parasitic invertebrate pest.

In a further aspect the invention provides a method of treating ananimal suffering from a parasitic invertebrate pest comprisingadministering to the animal a pesticidally effective amount of acompound of the invention. In a further aspect the invention relates toa compound of the invention for use in treating an animal suffering froma parasitic invertebrate pest. In a further aspect the invention relatesto use of a compound of the invention in the manufacture of a medicamentfor treating an animal suffering from a parasitic invertebrate pest.

In a further aspect, the invention provides a pharmaceutical compositioncomprising a compound of the invention and a pharmaceutically suitableexcipient.

The compounds of the invention may be used alone or in combination withone or more other biologically active ingredients.

In one aspect the invention provides a combination product comprising apesticidally effective amount of a component A and a pesticidallyeffective amount of component B wherein component A is a compound of theinvention and component B is a compound as described below.

The compounds of the invention may be used in combination withanthelmintic agents. Such anthelmintic agents include, compoundsselected from the macrocyclic lactone class of compounds such asivermectin, avermectin, abamectin, emamectin, eprinomectin, doramectin,selamectin, moxidectin, nemadectin and milbemycin derivatives asdescribed in EP-357460, EP-444964 and EP-594291. Additional anthelminticagents include semisynthetic and biosynthetic avermectin/milbemycinderivatives such as those described in U.S. Pat. No. 5,015,630,WO-9415944 and WO-9522552. Additional anthelmintic agents include thebenzimidazoles such as albendazole, cambendazole, fenbendazole,flubendazole, mebendazole, oxfendazole, oxibendazole, parbendazole, andother members of the class. Additional anthelmintic agents includeimidazothiazoles and tetrahydropyrimidines such as tetramisole,levamisole, pyrantel pamoate, oxantel or morantel. Additionalanthelmintic agents include flukicides, such as triclabendazole andclorsulon and the cestocides, such as praziquantel and epsiprantel.

The compounds of the invention may be used in combination withderivatives and analogues of the paraherquamide/marcfortine class ofanthelmintic agents, as well as the antiparasitic oxazolines such asthose disclosed in U.S. Pat, Nos. 5,478,855, 4,639,771 and DE-19520936.

The compounds of the invention may be used in combination withderivatives and analogues of the general class of dioxomorpholineantiparasitic agents as described in WO-9615121 and also withanthelmintic active cyclic depsipeptides such as those described inWO-9611945, WO-9319053, WO-9325543, EP-626375, EP-382173, WO-9419334,EP-382173, and EP-503538.

The compounds of the invention may be used in combination with otherectoparasiticides; for example, fipronil; pyrethroids; organophosphates;insect growth regulators such as lufenuron; ecdysone agonists such astebufenozide and the like; neonicotinoids such as imidacloprid and thelike.

The compounds of the invention may be used in combination with terpenealkaloids, for example those described in International PatentApplication Publication Numbers WO95/19363 or WO04/72086, particularlythe compounds disclosed therein.

Other examples of such biologically active compounds that the compoundsof the invention may be used in combination with include but are notrestricted to the following:

Organophosphates: acephate, azamethiphos, azinphos-ethyl,azinphos-methyl, bromophos, bromophos-ethyl, cadusafos, chlorethoxyphos,chlorpyrifos, chlorfenvinphos, chlormephos, demeton, demeton-S-methyl,demeton-S-methyl sulphone, dialifos, diazinon, dichlorvos, dicrotophos,dimethoate, disulfoton, ethion, ethoprophos, etrimfos, famphur,fenamiphos, fenitrothion, fensulfothion, fenthion, flupyrazofos,fonofos, formothion, fosthiazate, heptenophos, isazophos, isothioate,isoxathion, malathion, methacriphos, methamidophos, methidathion,methyl-parathion, mevinphos, monocrotophos, naled, omethoate,oxydemeton-methyl, paraoxon, parathion, parathion-methyl, phenthoate,phosalone, phosfolan, phosphocarb, phosmet, phosphamidon, phorate,phoxim, pirimiphos, pirimiphos-methyl, profenofos, propaphos,proetamphos, prothiofos, pyraclofos, pyridapenthion, quinalphos,sulprophos, temephos, terbufos, tebupirimfos, tetrachlorvinphos,thimeton, triazophos, trichlorfon, vamidothion.

Carbamates: alanycarb, aldicarb, 2-sec-butylphenyl methylcarbamate,benfuracarb, carbaryl, carbofuran, carbosulfan, cloethocarb,ethiofencarb, fenoxycarb, fenthiocarb, furathiocarb, HCN-801,isoprocarb, indoxacarb, methiocarb, methomyl,5-methyl-m-cumenylbutyryl(methyl)carbamate, oxamyl, pirimicarb,propoxur, thiodicarb, thiofanox, triazamate, UC-51717.

Pyrethroids: acrinathin, allethrin, alphametrin, 5-benzyl-3-furylmethyl(E)-(1R)-cis-2,2-dimethyl-3-(2-oxothiolan-3-ylidenemethyl)cyclopropanecarboxylate,bifenthrin, beta-cyfluthrin, cyfluthrin, a-cypermethrin, beta-cypermethrin, bioallethrin, bioallethrin((S)-cyclopentylisomer),bioresmethrin, bifenthrin, NCI-85193, cycloprothrin, cyhalothrin,cythithrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate,ethofenprox, fenfluthrin, fenpropathrin, fenvalerate, flucythrinate,flumethrin, fluvalinate (D isomer), imiprothrin, cyhalothrin,lambda-cyhalothrin, permethrin, phenothrin, prallethrin, pyrethrins(natural products), resmethrin, tetramethrin, transfluthrin,theta-cypermethrin, silafluofen, t-fluvalinate, tefluthrin,tralomethrin, Zeta-cypermethrin.

Arthropod growth regulators: a) chitin synthesis inhibitors:benzoylureas: chlorfluazuron, diflubenzuron, fluazuron, flucycloxuron,flufenoxuron, hexaflumuron, lufenuron, novaluron, teflubenzuron,triflumuron, buprofezin, diofenolan, hexythiazox, etoxazole,chlorfentazine; b) ecdysone antagonists: halofenozide, methoxyfenozide,tebufenozide; c) juvenoids: pyriproxyfen, methoprene (includingS-methoprene), fenoxycarb; d) lipid biosynthesis inhibitors:spirodiclofen.

Other antiparasitics: acequinocyl, amitraz, AKD-1022, ANS-118,azadirachtin, Bacillus thuringiensis, bensultap, bifenazate, binapacryl,bromopropylate, BTG-504, BTG-505, camphechlor, cartap, chlorobenzilate,chlordimeform, chlorfenapyr, chromafenozide, clothianidine, cyromazine,diacloden, diafenthiuron, DBI-3204, dinactin,dihydroxymethyldihydroxypyrrolidine, dinobuton, dinocap, endosulfan,ethiprole, ethofenprox, fenazaquin, flumite, MTI-800, fenpyroximate,fluacrypyrim, flubenzimine, flubrocythrinate, flufenzine, flufenprox,fluproxyfen, halofenprox, hydramethylnon, IKI-220, kanemite, NC-196,neem guard, nidinorterfuran, nitenpyram, SD-35651, WL-108477, pirydaryl,propargite, protrifenbute, pymethrozine, pyridaben, Buprofezinepyrimidifen, NC-1111, R-195,RH-0345, RH-2485, RYI-210, S-1283, S-1833,SI-8601, silafluofen, silomadine, spinosad, tebufenpyrad, tetradifon,tetranactin, thiacloprid, thiocyclam, thiamethoxam, tolfenpyrad,triazamate, triethoxyspinosyn, trinactin, verbutin, vertalec, YI-5301.

Fungicides: acibenzolar, aldimorph, ampropylfos, andoprim, azaconazole,azoxystrobin, benalaxyl, benomyl, bialaphos, blasticidin-S, Bordeauxmixture, bromuconazole, bupirimate, carpropamid, captafol, captan,carbendazim, chlorfenazole, chloroneb, chloropicrin, chlorothalonil,chlozolinate, copper oxychloride, copper salts, cyflufenamid, cymoxanil,cyproconazole, cyprodinil, cyprofuram, RH-7281, diclocymet,diclobutrazole, diclomezine, dicloran, difenoconazole, RP-407213,dimethomorph, domoxystrobin, diniconazole, diniconazole-M, dodine,edifenphos, epoxiconazole, famoxadone, fenamidone, fenarimol,fenbuconazole, fencaramid, fenpiclonil, fenpropidin, fenpropimorph,fentin acetate, fluazinam, fludioxonil, flumetover, flumorf/flumorlin,fentin hydroxide, fluoxastrobin, fluquinconazole, flusilazole,flutolanil, flutriafol, folpet, fosetyl-aluminium, furalaxyl,furametapyr, hexaconazole, ipconazole, iprobenfos, iprodione,isoprothiolane, kasugamycin, krsoxim-methyl, mancozeb, maneb, mefenoxam,mepronil, metalaxyl, metconazole, metominostrobin/fenominostrobin,metrafenone, myclobutanil, neo-asozin, nicobifen, orysastrobin,oxadixyl, penconazole, pencycuron, probenazole, prochloraz, propamocarb,propioconazole, proquinazid, prothioconazole, pyrifenox, pyraclostrobin,pyrimethanil, pyroquilon, quinoxyfen, spiroxamine, sulfur, tebuconazole,tetrconazole, thiabendazole, thifluzamide, thiophanate-methyl, thiram,tiadinil, triadimefon, triadimenol, tricyclazole, trifloxystrobin,triticonazole, validamycin, vinclozin.

Biological agents: Bacillus thuringiensis ssp aizawai, kurstaki,Bacillus thuringiensis delta endotoxin, baculovirus, entomopathogenicbacteria, virus and fungi.

Bactericides: chlortetracycline, oxytetracycline, streptomycin.

Other biological agents: enrofloxacin, febantel, penethamate, moloxicam,cefalexin, kanamycin, pimobendan, clenbuterol, omeprazole, tiamulin,benazepril, pyriprole, cefquinome, florfenicol, buserelin, cefovecin,tulathromycin, ceftiour, carprofen, metaflumizone, praziquarantel,triclabendazole.

When used in combination with other active ingredients, the compounds ofthe invention are preferably used in combination with the following(where “Tx” means a compound of formula (I), and in particular acompound selected from Tables 1 to 312, which may result in asynergistic combination with the given active ingredient): imidacloprid,enrofloxacin, praziquantel, pyrantel embonate, febantel, penethamate,moloxicam, cefalexin, kanamycin, pimobendan, clenbuterol, fipronil,ivermectin, omeprazole, tiamulin, benazepril, milbemycin, cyromazine,thiamethoxam, pyriprole, deltamethrin, cefquinome, florfenicol,buserelin, cefovecin, tulathromycin, ceftiour, selamectin, carprofen,metaflumizone, moxidectin, methoprene (including S-methoprene),clorsulon, pyrantel, amitraz, triclabendazole, avermectin, abamectin,emamectin, eprinomectin, doramectin, selamectin, nemadectin,albendazole, cambendazole, fenbendazole, flubendazole, mebendazole,oxfendazole, oxibendazole, parbendazole, tetramisole, levamisole,pyrantel pamoate, oxantel, morantel, triclabendazole, epsiprantel,fipronil, lufenuron, ecdysone or tebufenozide; more preferably,enrofloxacin, praziquantel, pyrantel 5 embonate, febantel, penethamate,moloxicam, cefalexin, kanamycin, pimobendan, clenbuterol, omeprazole,tiamulin, benazepril, pyriprole, cefquinome, florfenicol, buserelin,cefovecin, tulathromycin, ceftiour, selamectin, carprofen, moxidectin,clorsulon, pyrantel, eprinomectin, doramectin, selamectin, nemadectin,albendazole, cambendazole, fenbendazole, flubendazole, mebendazole,oxfendazole, oxibendazole, parbendazole, tetramisole, levamisole,pyrantel pamoate, oxantel, morantel, triclabendazole, epsiprantel,lufenuron or ecdysone; even more preferably enrofloxacin, praziquantel,pyrantel embonate, febantel, penethamate, moloxicam, cefalexin,kanamycin, pimobendan, clenbuterol, omeprazole, tiamulin, benazepril,pyriprole, cefquinome, florfenicol, buserelin, cefovecin, tulathromycin,ceftiour, selamectin, carprofen, moxidectin, clorsulon or pyrantel.

Examples of ratios of the compound of formula Ito any mixing partnerdescribed herein include 15 100:1 to 1:6000, 50:1 to 1:50, 20:1 to 1:20,even more especially from 10:1 to 1:10, 5:1 to 1:5, 2:1 to 1:2, 4:1 to2:1, 1:1, or 5:1, or 5:2, or 5:3, or 5:4, or 4:1, or 4:2, or 4:3, or3:1, or 3:2, or 2:1, or 1:5, or 2:5, or 3:5, or 4:5, or 1:4, or 2:4, or3:4, or 1:3, or 2:3, or 1:2, or 1:600, or 1:300, or 1:150, or 1:35, or2:35, or 4:35, or 1:75, or 2:75, or 4:75, or 1:6000, or 1:3000, or1:1500, or 1:350, or 2:350, or 4:350, or 1:750, or 2:750, or 4:750.Those mixing ratios are understood to include, on the one hand, ratiosby weight and also, on other hand, molar ratios.

Of particular note is a combination where the additional activeingredient has a different site of action from the compound of formulaI. In certain instances, a combination with at least one other parasiticinvertebrate pest control active ingredient having a similar spectrum ofcontrol but a different site of action will be particularly advantageousfor resistance management. Thus, a combination product of the inventionmay comprise a pesticidally effective amount of a compound of formula Iand pesticidally effective amount of at least one additional parasiticinvertebrate pest control active ingredient having a similar spectrum ofcontrol but a different site of action.

One skilled in the art recognizes that because in the environment andunder physiological conditions salts of chemical compounds are inequilibrium with their corresponding non salt forms, salts share thebiological utility of the non salt forms.

Thus a wide variety of salts of compounds of the invention (and activeingredients used in combination with the active ingredients of theinvention) may be useful for control of invertebrate pests and animalparasites. Salts include acid-addition salts with inorganic or organicacids such as hydrobromic, hydrochloric, nitric, phosphoric, sulfuric,acetic, butyric, fumaric, lactic, maleic, malonic, oxalic, propionic,salicylic, tartaric, 4-toluenesulfonic or valeric acids.

The compounds of the invention also include N-oxides. Accordingly, theinvention comprises combinations of compounds of the invention includingN-oxides and salts thereof and an additional active ingredient includingN-oxides and salts thereof.

The compositions for use in animal health may also contain formulationauxiliaries and additives, known to those skilled in the art asformulation aids (some of which may be considered to also function assolid diluents, liquid diluents or surfactants). Such formulationauxiliaries and additives may control: pH (buffers), foaming duringprocessing (antifoams such polyorganosiloxanes), sedimentation of activeingredients (suspending agents), viscosity (thixotropic thickeners),in-container microbial growth (antimicrobials), product freezing(antifreezes), color (dyes/pigment dispersions), wash-off (film formersor stickers), evaporation (evaporation retardants), and otherformulation attributes. Film formers include, for example, polyvinylacetates, polyvinyl acetate copolymers, polyvinylpyrrolidone-vinylacetate copolymer, polyvinyl alcohols, polyvinyl alcohol copolymers andwaxes. Examples of formulation auxiliaries and additives include thoselisted in McCutcheon 's Volume 2: Functional Materials, annualInternational and North American editions published by McCutcheon'sDivision, The Manufacturing Confectioner Publishing Co.; and PCTPublication WO 03/024222.

The compounds of the invention can be applied without other adjuvants,but most often application will be of a formulation comprising one ormore active ingredients with suitable carriers, diluents, andsurfactants and possibly in combination with a food depending on thecontemplated end use. One method of application involves spraying awater dispersion or refined oil solution of the combination products.Compositions with spray oils, spray oil concentrations, spreaderstickers, adjuvants, other solvents, and synergists such as piperonylbutoxide often enhance compound efficacy. Such sprays can be appliedfrom spray containers such as a can, a bottle or other container, eitherby means of a pump or by releasing it from a pressurized container,e.g., a pressurized aerosol spray can. Such spray compositions can takevarious forms, for example, sprays, mists, foams, fumes or fog. Suchspray compositions thus can further comprise propellants, foamingagents, etc. as the case may be. Of note is a spray compositioncomprising a pesticidally effective amount of a compound of theinvention and a carrier. One embodiment of such a spray compositioncomprises a pesticidally effective amount of a compound of the inventionand a propellant. Representative propellants include, but are notlimited to, methane, ethane, propane, butane, isobutane, butene,pentane, isopentane, neopentane, pentene, hydrofluorocarbons,chlorofluorocarbons, dimethyl ether, and mixtures of the foregoing. Ofnote is a spray composition (and a method utilizing such a spraycomposition dispensed from a spray container) used to control at leastone parasitic invertebrate pest selected from the group consisting ofmosquitoes, black flies, stable flies, deer flies, horse flies, wasps,yellow jackets, hornets, ticks, spiders, ants, gnats, and the like,including individually or in combinations.

The controlling of animal parasites includes controlling externalparasites that are parasitic to the surface of the body of the hostanimal (e.g., shoulders, armpits, abdomen, inner part of the thighs) andinternal parasites that are parasitic to the inside of the body of thehost animal (e.g., stomach, intestine, lung, veins, under the skin,lymphatic tissue). External parasitic or disease transmitting pestsinclude, for example, chiggers, ticks, lice, mosquitoes, flies, mitesand fleas. Internal parasites include heartworms, hookworms andhelminths. The compounds of the invention may be particularly suitablefor combating external parasitic pests. The compounds of the inventionmay be suitable for systemic and/or non-systemic control of infestationor infection by parasites on animals.

The compounds of the invention may be suitable for combating parasiticinvertebrate pests that infest animal subjects including those in thewild, livestock and agricultural working animals. Livestock is the termused to refer (singularly or plurally) to a domesticated animalintentionally reared in an agricultural setting to make produce such asfood or fiber, or for its labor; examples of livestock include cattle,sheep, goats, horses, pigs, donkeys, camels, buffalo, rabbits, hens,turkeys, ducks and geese (e.g., raised for meat, milk, butter, eggs,fur, leather, feathers and/or wool), cultured fish, honeybees. Bycombating parasites, fatalities and performance reduction (in terms ofmeat, milk, wool, skins, eggs, etc.) 10 are reduced, so that applyingthe compounds of the invention allows more economic and simple husbandryof animals.

By controlling these pests it is intended to reduce deaths and improveperformance (in the case of meat, milk, wool, hides, eggs, honey and thelike) and health of the host animal. Also, controlling parasites mayhelp to prevent the transmittance of infectious agents, the term“controlling” referring to the veterinary field, meaning that the activecompounds are effective in reducing the incidence of the respectiveparasite in an animal infected with such parasites to innocuous levels,e.g. the active compound is effective in killing the respectiveparasite, inhibiting its growth, or inhibiting its proliferation.

The compounds of the invention may be suitable for combating parasiticinvertebrate pests that infest companion animals and pets (e.g., dogs,cats, pet birds and aquarium fish), research and experimental animals(e.g., hamsters, guinea pigs, rats and mice), as well as animals raisedfor/in zoos, wild habitats and/or circuses.

In an embodiment of this invention, the animal is preferably avertebrate, and more preferably a mammal, avian or fish. In a particularembodiment, the animal subject is a mammal (including great apes, suchas humans). Other mammalian subjects include primates (e.g., monkeys),bovine (e.g., cattle or dairy cows), porcine (e.g., hogs or pigs), ovine(e.g., goats or sheep), equine (e.g., horses), canine (e.g., dogs),feline (e.g., house cats), camels, deer, donkeys, buffalos, antelopes,rabbits, and rodents (e.g., guinea pigs, squirrels, rats, mice, gerbils,and hamsters). Avians include Anatidae (swans, ducks and geese),Columbidae (e.g., doves and pigeons), Phasianidae (e.g., partridges,grouse and turkeys), Thesienidae (e.g., domestic chickens), Psittacines(e.g., parakeets, macaws, and parrots), game birds, and ratites (e.g.,ostriches).

Birds treated or protected by the compounds of the invention can beassociated with either commercial or noncommercial aviculture. Theseinclude Anatidae, such as swans, geese, and ducks, Columbidae, such asdoves and domestic pigeons, Phasianidae, such as partridge, grouse andturkeys, Thesienidae, such as domestic chickens, and Psittacines, suchas parakeets, macaws and parrots raised for the pet or collector market,among others.

For purposes of the present invention, the term “fish” is understood toinclude without limitation, the Teleosti grouping of fish, i.e.,teleosts. Both the Salmoniformes order (which includes the Salmonidaefamily) and the Perciformes order (which includes the Centrarchidaefamily) are contained within the Teleosti grouping. Examples ofpotential fish recipients include the Salmonidae, Serranidae, Sparidae,Cichlidae, and Centrarchidae, among others.

Other animals are also contemplated to benefit from the inventivemethods, including marsupials (such as kangaroos), reptiles (such asfarmed turtles), and other economically important domestic animals forwhich the inventive methods are safe and effective in treating orpreventing parasite infection or infestation.

Examples of parasitic invertebrate pests controlled by administering apesticidally effective amount of the compounds of the invention to ananimal to be protected include ectoparasites (arthropods, acarines,etc.) and endoparasites (helminths, e.g., nematodes, trematodes,cestodes, acanthocephalans, etc. and protozoae, such as coccidia).

The disease or group of diseases described generally as helminthiasis isdue to infection of an animal host with parasitic worms known ashelminths. The term ‘helminths’ is meant to include nematodes,trematodes, cestodes and acanthocephalans. Helminthiasis is a prevalentand serious economic problem with domesticated animals such as swine,sheep, horses, cattle, goats, dogs, cats and poultry.

Among the helminths, the group of worms described as nematodes causeswidespread and at times serious infection in various species of animals.

Nematodes that are contemplated to be treated by the compounds of theinvention include, without limitation, the following genera:Acanthocheilonema, Aelurostrongylus, Ancylostoma, Angiostrongylus,Ascaridia, Ascaris, Brugia, Bunostomum, Capillaria, Chabertia, Cooperia,Crenosoma, Dictyocaulus, Dioctophyme, Dipetalonema, Diphyllobothrium,Dirofilaria, Dracunculus, Enterobius, Filaroides, Haemonchus, Heterakis,Lagochilascaris, Loa, Mansonella, Muellerius, Necator, Nematodirus,Oesophagostomum, Ostertagia, Oxyuris, Parafilaria, Parascaris,Physaloptera, Protostrongylus, Setaria, Spirocerca, Stephanofilaria,Strongyloides, Strongylus, Thelazia, Toxascaris, Toxocara, Trichinella,Trichonema, Trichostrongylus, Trichuris, Uncinaria and Wuchereria.

Of the above, the most common genera of nematodes infecting the animalsreferred to above are Haemonchus, Trichostrongylus, Ostertagia,Nematodirus, Cooperia, Ascaris, Bunostomum, Oesophagostomum, Chabertia,Trichuris, Strongylus, Trichonema, Dictyocaulus, Capillaria, Heterakis,Toxocara, Ascaridia, Oxyuris, Ancylostoma, Uncinaria, Toxascaris andParascaris. Certain of these, such as Nematodirus, Cooperia andOesophagostomum attack primarily the intestinal tract while others, suchas Haemonchus and Ostertagia, are more prevalent in the stomach whileothers such as Dictyocaulus are found in the lungs. Still otherparasites may be located in other tissues such as the heart and bloodvessels, subcutaneous and lymphatic tissue and the like.

Trematodes that are contemplated to be treated by the invention and bythe inventive methods include, without limitation, the following genera:Alaria, Fasciola, Nanophyetus, Opisthorchis, Paragonimus andSchistosoma.

Cestodes that are contemplated to be treated by the invention and by theinventive methods include, without limitation, the following genera:Diphyllobothrium, Diplydium, Spirometra and Taenia.

The most common genera of parasites of the gastrointestinal tract ofhumans are Ancylostoma, Necator, Ascaris, Strongy hides, Trichinella,Capillaria, Trichuris and Enterobius. Other medically important generaof parasites which are found in the blood or other tissues and organsoutside the gastrointestinal tract are the filarial worms such asWuchereria, Brugia, Onchocerca and Loa, as well as Dracunculus and extraintestinal stages of the intestinal worms Strongyloides and Trichinella.

Numerous other helminth genera and species are known to the art, and arealso contemplated to be treated by the compounds of the invention. Theseare enumerated in great detail in Textbook of Veterinary ClinicalParasitology, Volume 1, Helminths, E. J. L. Soulsby, F. A. Davis Co.,Philadelphia, Pa.; Helminths, Arthropods and Protozoa, (6^(th)Edition ofMonnig's Veterinary Helminthology and Entomology), E. J. L. Soulsby,Williams and Wilkins Co., Baltimore, Md.

The compounds of the invention may be effective against a number ofanimal ectoparasites (e.g., arthropod ectoparasites of mammals and birdsin particular insects such as flies (stinging and licking), parasiticfly larvae, lice, hair lice, bird lice, fleas and the like; or acarids,such as ticks, for examples hard ticks or soft ticks, or mites, such asscab mites, harvest mites, bird mites and the like).

Insect and acarine pests include, e.g., biting insects such as flies andmosquitoes, mites, ticks, lice, fleas, true bugs, parasitic maggots, andthe like.

Adult flies include, e.g., the horn fly or Haematobia irritans, thehorse fly or Tabanus spp., the stable fly or Stomoxys calcitrans, theblack fly or Simulium spp., the deer fly or Chrysops spp., the louse flyor Melophagus ovinus, and the tsetse fly or Glossina spp. Parasitic flymaggots include, e.g., the bot fly (Oestrus ovis and Cuterebra spp.),the blow fly or Phaenicia spp., the screwworm or Cochliomyiahominivorax, the cattle grub or Hypoderma spp., the fleeceworm and theGastrophilus of horses. Mosquitoes include, for example, Culex spp.,Anopheles spp. and Aedes spp.

Mites include Mesostigmalphatalpha spp. e.g., mesostigmatids such as thechicken mite, Dermalphanyssus galphallinalphae; itch or scab mites suchas Sarcoptidae spp. for example, Salpharcoptes scalphabiei; mange mitessuch as Psoroptidae spp. including Chorioptes bovis and Psoroptes ovis;chiggers e.g., Trombiculidae spp. for example the North Americanchigger, Trombiculalpha alphalfreddugesi.

Ticks include, e.g., soft-bodied ticks including Argasidae spp. forexample Argalphas spp. and Ornithodoros spp.; hard-bodied ticksincluding Ixodidae spp., for example Rhipicephalphalus sanguineus,Dermacentor variabilis, Dermacentor andersoni, Amblyomma americanum,Ixodes scapularis and other Rhipicephalus spp. (including the formerBoophilus genera).

Lice include, e.g., sucking lice, e.g., Menopon spp. and Bovicola spp.;biting lice, e.g., Haematopinus spp., Linognathus spp. and Solenopotesspp.

Fleas include, e.g., Ctenocephalides spp., such as dog flea(Ctenocephalides canis) and cat flea (Ctenocephalides felis); Xenopsyllaspp. such as oriental rat flea (Xenopsylla cheopis); and Pulex spp. suchas human flea (Pulex irritans).

True bugs include, e.g., Cimicidae or e.g., the common bed bug (Cimexlectularius); Triatominae spp. including triatomid bugs also known askissing bugs; for example Rhodnius prolixus and Triatoma spp.

Generally, flies, fleas, lice, mosquitoes, gnats, mites, ticks andhelminths cause tremendous losses 5 to the livestock and companionanimal sectors. Arthropod parasites also are a nuisance to humans andcan vector disease-causing organisms in humans and animals.

Numerous other parasitic invertebrate pests are known to the art, andare also contemplated to be treated by the compounds of the invention.These are enumerated in great detail in Medical and VeterinaryEntomology, D. S. Kettle, John Wiley AND Sons, New York and Toronto;Control of Arthropod Pests of Livestock: A Review of Technology, R. O.Drummand, J. E. George, and S. E. Kunz, CRC Press, Boca Raton, Fla.

The compounds of the invention may also be effective againstectoparasites, e.g. insects such as flies (stinging and licking),parasitic fly larvae, lice, hair lice, bird lice, fleas and the like; oracarids, such as ticks, for examples hard ticks or soft ticks, or mites,such as scab mites, harvest mites, bird mites and the like. Theseinclude e.g. flies such as Haematobia (Lyperosia) irritans (horn fly),Simulium spp. (blackfly), Glossina spp. (tsetse flies), Hydrotaeairritans (head fly), Musca autumnalis (face fly), Musca domestica (housefly), Morellia simplex (sweat fly), Tabanus spp. (horse fly), Hypodermabovis, Hypoderma lineatum, Lucilia sericata, Lucilia cuprina (greenblowfly), Calliphora spp. (blowfly), Protophormia spp., Oestrus ovis(nasal botfly), Culicoides spp. (midges), Hippobosca equine,Gastrophilus intestinalis, Gastrophilus haemorrhoidalis and Gastrophilusnasalis; lice such as Bovicola (Damalinia) bovis, Bovicola equi,Haematopinus asini, Felicola subrostratus, Heterodoxus spiniger,Lignonathus setosus and Trichodectes canis; keds such as Melophagusovinus; and mites such as Psoroptes spp., Sarcoptes scabei, Chorioptesbovis, Demodex equi, Cheyletiella spp., Notoedres cati, Trombicula spp.and Otodectes cyanotis (ear mites).

Examples of species of animal health pesets include those from the orderof the Anoplurida, for example Haematopinus spp., Linognathus spp.,Pediculus spp., Phtirus spp., Solenopotes spp.; particular examples are:Linognathus setosus, Linognathus vituli, Linognathus ovillus,Linognathus oviformis, Linognathus pedalis, Linognathus stenopsis,Haematopinus asini macrocephalus, Haematopinus eurysternus, Haematopinussuis, Pediculus humanus capitis, Pediculus humanus corporis, Phylloeravastatrix, Phthirus pubis, Solenopotes capillatus; from the order of theMallophagida and the suborders Amblycerina and Ischnocerina, for exampleTrimenopon spp., Menopon spp., Trinoton spp., Bovicola spp.,Werneckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp.,Felicola spp.; particular examples are: Bovicola bovis, Bovicola ovis,Bovicola limbata, Damalina bovis, Trichodectes canis, Felicolasubrostratus, Bovicola caprae, Lepikentron ovis, Werneckiella equi; fromthe order of the Diptera and the suborders Nematocerina andBrachycerina, for example Aedes spp., Anopheles spp., Culex spp.,Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp.,Culicoides spp., Chrysops spp., Odagmia spp., Wilhelmia spp., Hybomitraspp., Atylotus spp., Tabanus spp., Haematopota spp., Philipomyia spp.,Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp.,Morellia spp., Fannia spp., Glossina spp., Calliphora spp., Luciliaspp., Chrysomyia spp., Wohlfahrtia spp., Sarcophaga spp., Oestrus spp.,Hypoderma spp., Gasterophilus spp., Hippobosca spp., Lipoptena spp.,Melophagus spp., Rhinoestrus spp., Tipula spp.; particular examples are:Aedes aegypti, Aedes albopictus, Aedes taeniorhynchus, Anophelesgambiae, Anopheles maculipennis, Calliphora erythrocephala, Chrysozonapluvialis, Culex quinquefasciatus, Culex pipiens, Culex tarsalis, Fanniacanicularis, Sarcophaga carnaria, Stomoxys calcitrans, Tipula paludosa,Lucilia cuprina, Lucilia sericata, Simulium reptans, Phlebotomuspapatasi, Phlebotomus longipalpis, Odagmia ornata, Wilhelmia equina,Boophthora erythrocephala, Tabanus bromius, Tabanus spodopterus, Tabanusatratus, Tabanus sudeticus, Hybomitra ciurea, Chrysops caecutiens,Chrysops relictus, Haematopota pluvialis, Haematopota italica, Muscaautumnalis, Musca domestica, Haematobia irritans irritans, Haematobiairritans exigua, Haematobia stimulans, Hydrotaea irritans, Hydrotaeaalbipuncta, Chrysomya chloropyga, Chrysomya bezziana, Oestrus ovis,Hypoderma bovis, Hypoderma lineaturn, Przhevalskiana silenus, Dermatobiahominis, Melophagus ovinus, Lipoptena capreoli, Lipoptena cervi,Hippobosca variegata, Hippobosca equina, Gasterophilus intestinalis,Gasterophilus haemorroidalis, Gasterophilus inermis, Gasterophilusnasalis, Gasterophilus nigricornis, Gasterophilus pecorum, Braula coeca;from the order of the Siphonapterida, for example Pulex spp.,Ctenocephalides spp., Tunga spp., Xenopsylla spp., Ceratophyllusl spp.;particular examples are: Ctenocephalides canis, Ctenocephalides felis,Pulex irritans, Tunga penetrans, Xenopsylla cheopis; from the order ofthe Heteropterida, for example Cimex spp., Triatoma spp., Rhodnius spp.,Panstrongylus spp; from the order of the Blattarida, for example Blattaorientalis, Periplaneta americana, Blattela germanica, Supella spp.(e.g. Suppella longipalpa); from the subclass of the Acari (Acarina) andthe orders of the Meta- and Mesostigmata, for example Argas spp.,Ornithodorus spp., Otobius spp., Ixodes spp., Amblyomma spp.,Rhipicephalus (Boophilus) spp Dermacentor spp., Haemophysalis spp.,Hyalomma spp., Dermanyssus spp., Rhipicephalus spp. (the original genusof multi host ticks) Ornithonyssus spp., Pneumonyssus spp., Raillietiaspp., Pneumonyssus spp., Sternostoma spp., Varroa spp., Acarapis spp.;particular examples are: Argas persicus, Argas reflexus, Ornithodorusmoubata, Otobius megnini, Rhipicephalus (Boophilus) microplus,Rhipicephalus (Boophilus) decoloratus, Rhipicephalus (Boophilus)annulatus, Rhipicephalus (Boophilus) calceratus, Hyalomma anatolicum,Hyalomma aegypticum, Hyalomma marginatum, Hyalomma transiens,Rhipicephalus evertsi, Ixodes ricinus, Ixodes hexagonus, Ixodescanisuga, Ixodes pilosus, Ixodes rubicundus, Ixodes scapularis, Ixodesholocyclus, Haemaphysalis concinna, Haemaphysalis punctata,Haemaphysalis cinnabarina, Haemaphysalis otophila, Haemaphysalis leachi,Haemaphysalis longicorni, Dermacentor marginatus, Dermacentorreticulatus, Dermacentor pictus, Dermacentor albipictus, Dermacentorandersoni, Dermacentor variabilis, Hyalomma mauritanicum, Rhipicephalussanguineus, Rhipicephalus bursa, Rhipicephalus appendiculatus,Rhipicephalus capensis, Rhipicephalus turanicus, Rhipicephaluszambeziensis, Amblyomma americanum, Amblyomma variegatum, Amblyommamaculatum, Amblyomma hebraeum, Amblyomma cajennense, Dermanyssusgallinae, Ornithonyssus bursa, Ornithonyssus sylviarum, Varroajacobsoni; from the order of the Actinedida (Prostigmata) and Acaridida(Astigmata), for example Acarapis spp., Cheyletiella spp.,Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp.,Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp.,Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp.,Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp.,Knemidocoptes spp., Cytodites spp., Laminosioptes spp.; particularexamples are: Cheyletiella yasguri, Cheyletiella blakei, Demodex canis,Demodex bovis, Demodex ovis, Demodex caprae, Demodex equi, Demodexcaballi, Demodex suis, Neotrombicula autumnalis, Neotrombicula desaleri,Neoschongastia xerothermobia, Trombicula akamushi, Otodectes cynotis,Notoedres cati, Sarcoptis canis, Sarcoptes bovis, Sarcoptes ovis,Sarcoptes rupicaprae (S. caprae), Sarcoptes equi, Sarcoptes suis,Psoroptes ovis, Psoroptes cuniculi, Psoroptes equi, Chorioptes bovis,Psoergates ovis, Pneumonyssoidic mange, Pneumonyssoides caninum,Acarapis woodi; Gasterophilus spp., Stomoxys spp., Trichodectes spp.,Rhodnius spp., Ctenocephalides canis, Cimx lecturius, Ctenocephalidesfelis, Lucilia cuprina; examples of acari include Ornithodoros spp.,Ixodes spp., Boophilus spp.

Treatments of the invention are by conventional means such as by enteraladministration in the form of, for example, tablets, capsules, drinks,drenching preparations, granulates, pastes, boli, feed-throughprocedures, or suppositories; or by parenteral administration, such as,for example, by injection (including intramuscular, subcutaneous,intravenous, intraperitoneal) or implants; or by nasal administration;or by dermal application in the form of, for example, bathing ordipping, spraying, pouring-on and spotting-on, washing, dusting, andwith the aid of active-compound-comprising shaped articles such ascollars, ear tags, tail tags, limb bands, halters, marking devices andthe like.

When compounds of the invention are applied in combination with anadditional biologically active ingredient, they may be administeredseparately e.g. as separate compositions. In this case, the biologicallyactive ingredients may be administered simultaneously or sequentially.Alternatively, the biologically active ingredients may be components ofone composition.

The compounds of the invention may be administered in a controlledrelease form, for example in subcutaneous or orally adminstered slowrelease formulations.

Typically a parasiticidal composition according to the present inventioncomprises a compound of the invention, optionally in combination with anadditional biologically active ingredient, or N-oxides or salts thereof,with one or more pharmaceutically or veterinarily acceptable carrierscomprising excipients and auxiliaries selected with regard to theintended route of administration (e.g., oral or parenteraladministration such as injection) and in accordance with standardpractice. In addition, a suitable carrier is selected on the basis ofcompatibility with the one or more active ingredients in thecomposition, including such considerations as stability relative to pHand moisture content. Therefore of note are compounds of the inventionfor protecting an animal from an invertebrate parasitic pest comprisinga parasitically effective amount of a compound of the invention,optionally in combination with an additional biologically activeingredient and at least one carrier.

For parenteral administration including intravenous, intramuscular andsubcutaneous injection, the compounds of the invention can be formulatedin suspension, solution or emulsion in oily or aqueous vehicles, and maycontain adjuncts such as suspending, stabilizing and/or dispersingagents.

The compounds of the invention may also be formulated for bolusinjection or continuous infusion. Pharmaceutical compositions forinjection include aqueous solutions of water-soluble forms of activeingredients (e.g., a salt of an active compound), preferably inphysiologically compatible buffers containing other excipients orauxiliaries as are known in the art of pharmaceutical formulation.Additionally, suspensions of the active compounds may be prepared in alipophilic vehicle. Suitable lipophilic vehicles include fatty oils suchas sesame oil, synthetic fatty acid esters such as ethyl oleate andtriglycerides, or materials such as liposomes.

Aqueous injection suspensions may contain substances that increase theviscosity of the suspension, such as sodium carboxymethyl cellulose,sorbitol, or dextran. Formulations for injection may be presented inunit dosage form, e.g., in ampoules or in multi-dose containers.Alternatively, the active ingredient may be in powder form forconstitution with a suitable vehicle, e.g., sterile, pyrogen-free water,before use.

In addition to the formulations described supra, the compounds of theinvention may also be formulated as a depot preparation. Such longacting formulations may be administered by implantation (for example,subcutaneously or intramuscularly) or by intramuscular or subcutaneousinjection.

The compounds of the invention may be formulated for this route ofadministration with suitable polymeric or hydrophobic materials (forinstance, in an emulsion with a pharmacologically acceptable oil), withion exchange resins, or as a sparingly soluble derivative such as,without limitation, a sparingly soluble salt.

For administration by inhalation, the compounds of the invention can bedelivered in the form of an aerosol spray using a pressurized pack or anebulizer and a suitable propellant, e.g., without limitation,dichlorodifluoromethane, trichlorofluoromethane,dichlorotetrafluoroethane or carbon dioxide. In the case of apressurized aerosol, the dosage unit may be controlled by providing avalve to deliver a metered amount. Capsules and cartridges of, forexample, gelatin for use in an inhaler or insufflator may be formulatedcontaining a powder mix of the compound and a suitable powder base suchas lactose or starch.

The compounds of the invention may have favourable pharmacokinetic andpharmacodynamic properties providing systemic availability from oraladministration and ingestion. Therefore after ingestion by the animal tobe protected, parasiticidally effective concentrations of a compound ofthe invention in the bloodstream may protect the treated animal fromblood-sucking pests such as fleas, ticks and lice. Therefore of note isa composition for protecting an animal from an invertebrate parasitepest in a form for oral administration (i.e. comprising, in addition toa parasiticidally effective amount of a compound of the invention, oneor more carriers selected from binders and fillers suitable for oraladministration and feed concentrate carriers).

For oral administration in the form of solutions (the most readilyavailable form for absorption), emulsions, suspensions, pastes, gels,capsules, tablets, boluses, powders, granules, rumen-retention andfeed/water/lick blocks, the compounds of the invention can be formulatedwith binders/fillers known in the art to be suitable for oraladministration compositions, such as sugars and sugar derivatives (e.g.,lactose, sucrose, mannitol, sorbitol), starch (e.g., maize starch, wheatstarch, rice starch, potato starch), cellulose and derivatives (e.g.,methylcellulose, carboxymethylcellulose, ethylhydroxycellulose), proteinderivatives (e.g., zein, gelatin), and synthetic polymers (e.g.,polyvinyl alcohol, polyvinylpyrrolidone). If desired, lubricants (e.g.,magnesium stearate), disintegrating agents (e.g., cross-linkedpolyvinylpyrrolidinone, agar, alginic acid) and dyes or pigments can beadded. Pastes and gels often also contain adhesives (e.g., acacia,alginic acid, bentonite, cellulose, xanthan gum, colloidal magnesiumaluminum silicate) to aid in keeping the composition in contact with theoral cavity and not being easily ejected.

In one embodiment a composition of the present invention is formulatedinto a chewable and/or edible product (e.g., a chewable treat or edibletablet). Such a product would ideally have a taste, texture and/or aromafavored by the animal to be protected so as to facilitate oraladministration of the compounds of the invention.

If the parasiticidal compositions are in the form of feed concentrates,the carrier is typically selected from high-performance feed, feedcereals or protein concentrates. Such feed concentrate-containingcompositions can, in addition to the parasiticidal active ingredients,comprise additives promoting animal health or growth, improving qualityof meat from animals for slaughter or otherwise useful to animalhusbandry.

These additives can include, for example, vitamins, antibiotics,chemotherapeutics, bacteriostats, fungistats, coccidiostats andhormones.

The compound of the invention may also be formulated in rectalcompositions such as suppositories or retention enemas, using, e.g.,conventional suppository bases such as cocoa butter or other glycerides.

The formulations for the method of this invention may include anantioxidant, such asBHT (butylated hydroxytoluene). The antioxidant isgenerally present in amounts of at 0.1-5 percent (wt/vol). Some of theformulations require a solubilizer, such as oleic acid, to dissolve theactive agent, particularly if spinosad is included. Common spreadingagents used in these pour-on formulations include isopropyl myristate,isopropyl palmitate, caprylic/capric acid esters of saturated C₁₂-C₁₈fatty alcohols, oleic acid, oleyl ester, ethyl oleate, triglycerides,silicone oils and dipropylene glycol methyl ether. The pour-onformulations for the method of this invention are prepared according toknown techniques. Where the pour-on is a solution, theparasiticide/insecticide is mixed with the carrier or vehicle, usingheat and stirring if required. Auxiliary or additional ingredients canbe added to the mixture of active agent and carrier, or they can bemixed with the active agent prior to the addition of the carrier.Pour-on formulations in the form of emulsions or suspensions aresimilarly prepared using known techniques.

Other delivery systems for relatively hydrophobic pharmaceuticalcompounds may be employed. Liposomes and emulsions are well-knownexamples of delivery vehicles or carriers for hydrophobic drugs. Inaddition, organic solvents such as dimethylsulfoxide may be used, ifneeded.

The rate of application required for effective parasitic invertebratepest control (e.g. “pesticidally effective amount”) will depend on suchfactors as the species of parasitic invertebrate pest to be controlled,the pest's life cycle, life stage, its size, location, time of year,host crop or animal, feeding behavior, mating behavior, ambientmoisture, temperature, and the like. One skilled in the art can easilydetermine the pesticidally effective amount necessary for the desiredlevel of parasitic invertebrate pest control.

In general for veterinary use, the compounds of the invention areadministered in a pesticidally effective amount to an animal,particularly a homeothermic animal, to be protected from parasiticinvertebrate pests.

A pesticidally effective amount is the amount of active ingredientneeded to achieve an observable effect diminishing the occurrence oractivity of the target parasitic invertebrate pest. One skilled in theart will appreciate that the pesticidally effective dose can vary forthe various compounds and compositions useful for the method of thepresent invention, the desired pesticidal effect and duration, thetarget parasitic invertebrate pest species, the animal to be protected,the mode of application and the like, and the amount needed to achieve aparticular result can be determined through simple experimentation.

For oral or parenteral administration to animals, a dose of thecompositions of the present invention administered at suitable intervalstypically ranges from about 0.01 mg/kg to about 100 mg/kg, andpreferably from about 0.01 mg/kg to about 30 mg/kg of animal bodyweight.

Suitable intervals for the administration of the compositions of thepresent invention to animals range from about daily to about yearly. Ofnote are administration intervals ranging from about weekly to aboutonce every 6 months. Of particular note are monthly adminstrationintervals (i.e. administering the compounds to the animal once everymonth).

The Following Examples Illustrate, but do not Limit, the Invention.

The compounds of the invention can be distinguished from known compoundsby virtue of greater efficacy at low application rates, which can beverified by the person skilled in the art using the experimentalprocedures outlined in the Examples, using lower application rates ifnecessary, for example 50 ppm, 12.5 ppm, 6 ppm, 3 ppm, 1.5 ppm or 0.8ppm.

The following abbreviations were used in this section: DMF:dimethylformamide; THF: tetrahydrofuran; EtOAc: ethyl acetate;s=singlet; bs=broad singlet; d=doublet; dd=double doublet; dt=doubletriplet; t=triplet, tt=triple triplet, q=quartet, sept=septet;m=multiplet; Me=methyl; Et=ethyl; Pr=propyl; Bu=butyl; M.p.=meltingpoint; RT=retention time, [M+H]⁺=molecular mass of the molecular cation,[M−H]⁻=molecular mass of the molecular anion.

The following LC-MS methods were used to characterize the compounds:

Method A MS ACQUITY SQD Mass Spectrometer from Waters (Single quadrupolemass spectrometer) Ionisation method: Electrospray Polarity: positiveions Capillary (kV) 3.00, Cone (V) 20.00, Extractor (V) 3.00, SourceTemperature (° C.) 150, Desolvation Temperature (° C.) 400, Cone GasFlow (L/Hr) 60, Desolvation Gas Flow (L/Hr) 700 Mass range: 100 to 800Da DAD Wavelength range (nm): 210 to 400 LC Method Waters ACQUITY UPLCwith the following HPLC gradient conditions (Solvent A: Water/Methanol9:1, 0.1% formic acid and Solvent B: Acetonitrile, 0.1% formic acid)Time (min) A % B % Flow (ml/min) 0 100 0 0.75 2.5 0 100 0.75 2.8 0 1000.75 3.0 100 0 0.75

Method F CHIRAL Alliance 2695 HPLC from Waters: solvent degasser, HPLCbinary pump, heated column compartment and diode-array detector Column:Chiralpak IA, length (mm) 250, internal diameter (mm) 4.6, particle size(μ) 5, wavelength (nm): 270 nm, temperature (° C.) 30, solvent:Isocratic isopropyl alcohol: heptanes 10:90, injection volume 50 uL,flow (ml/min) 1.

EXAMPLE 1[2-bromo-4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]phenyl]sulfanylmethanesulfonamide

Step A: 1-(3-bromo-4-tert-butylsulfanyl-phenyl)ethanone

In a mechanically stirred reactor was charged dimethylformamide (350mL), 1-(4-fluoro-3-bromo-phenyl)-ethanone (30 g), potassium carbonate(29 g) followed by tert-butylthiol (18.7 g). The resulting suspensionwas heated to 50° C. for 4 hours. The mixture was then cooled to roomtemperature and poured in brine (1 L), and the aqueous phase wasextracted three times with ethyl acetate. The combined organic phaseswere washed with brine and dried over MgSO₄. The solvents were removedto leave the desired compound (40 g). LCMS (Method A) RT 1.11 min.[M+H]⁺277-279. ¹H NMR (400 MHz, CDCl₃) 1.40 (s, 9H), 2.59 (s, 3H), 7.70(d, 1H), 7.71 (dd, 1H), 8.19 (d, 1H).

Step B:(E)-1-(3-bromo-4-tert-butylsulfanyl-phenyl)-3-(3,5-dichlorophenyl)-4,4,4-trifluoro-but-2-en-1-one

A suspension of 1-(3-bromo-4-tert-butylsulfanyl-phenyl)ethanone (Step A,25.0 g), 1-(3,5-dichloro-phenyl)-2,2,2-trifluoro-ethanone (23.3 g),potassium carbonate (13.5 g), and triethylamine (1.2 ml) in1,2-dichloroethane (500 ml), was heated at 85° C. for 16 hours. Thereaction mixture was cooled to room temperature, partitioned betweendichloromethane and water. The aqueous layer was separated, extractedwith dichloromethane and the combined organic layers were dried overMgSO₄ and the solvent removed in vacuo. The residue (52.5 g) waspurified by column chromatography on SiO₂ with heptane/EtOAc (95:5) toafford the title product (22.8 g) as a yellow solid. LCMS (Method A) RT1.37 min, [M+OH]⁺527/529/531; ¹H-NMR (CDCl₃, 400 MHz): 1.39 (s, 9H),7.10 (s, 2H), 7.37 (m, 2H), 7.64 (m, 2H), 8.01 (s, 1H). ¹⁹F-NMR (CDCl₃,400 MHz): −67.2.

Step C:3-(3-Bromo-4-tert-butylsulfanyl-phenyl)-5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazole

To a solution of(E)-1-(3-bromo-4-tert-butylsulfanyl-phenyl)-3-(3,5-dichlorophenyl)-4,4,4-trifluoro-but-2-en-1-one(prepared as described in Step B, 7.4 g) in 1,2-dichloroethane (37 ml)was added tetrabutylammonium bomide (1.4 g). The reaction mixture wascooled at 0° C. then hydroxylamine (50% 5 in water, 1.8 ml) and sodiumhydroxide (15 g) were added simultaneously. The reaction was stirred 0°C. for 25 min and then brought back to room temperature. The mixture wasdiluted with water and extracted with dichloromethane several times; thecombined organic layers were neutralized with 4N hydrochloric acidsolution dried over MgSO₄ and the solvent evaporated under reducedpressure to obtain a solid, which was purified by column chromatography,eluted with heptane/EtOAc to afford the title product (4.2 g) as acolourless solid, which was used as such for the next step.

Step D:2-bromo-4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]benzenethiol

To a solution of3-(3-bromo-4-tert-butylsulfanyl-phenyl)-5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazole(3.8 g) in toluene (19 mL) was added toluene-4-sulfonic acid (1.3 g) andthe reaction was heated at a 110° C. overnight. The reaction was cooleddown to room temperature and diluted in dichloromethane and washed withan aqueous saturated NaHCO₃ solution. The organic phase was dried overMgSO₄ and the solvents removed in vacuo to yield the crude product (5.3g). The crude product was washed with hexane to yield the title compoundas a solid (3.4 g). LCMS (Method A) RT 1.33 min, [M−H]⁻468/470/472;¹H-NMR (CDCl₃, 400 MHz): 3.64 (d, 1H), 4.03 (d, 1H), 4.17 (s, 1H, SH),7.39 (d, 1H), 7.41 (m, 2H), 7.49 (m, 3H), 7.78 (d, 1H).

Step E:[2-bromo-4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]phenyl]sulfanylmethanesulfonamide

To a solution of2-bromo-4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]benzenethiol(0.47 g) in N,N-dimethylformamide (7 ml) at room temperature was addedpotassium carbonate (0.2 g) then a solution of chloromethanesulfonamide(0.14 g) in N,N-dimethylformamide (3 ml); the resulting solution wasstirred for 2 hours at room temperature, diluted with ethyl acetate (15ml) then washed with 1N HCl solution (5 ml). The combined organic layerswere washed with water then brine and dried over anhydrous sodiumsulfate, filtered and concentrated under reduced pressure to dryness toafford a crude residue (275 mg), which was purified with CombiflashRf200, (column of 5 g), eluted with heptane/EtOAc to afford the titleproduct (0.275 g) as a white solid. LCMS (Method A) RT 1.14 min,[M+H]⁺563/565. ¹H-NMR (CDCl₃, 400 MHz): 3.60 (d, 1H), 3.98 (d, 1H), 4.35(s, 2H), 4.70 (br s, 2H), 7.36 (t, 1H), 7.41 (d, 2H), 7.52 (dd, 1H),7.60 (d, 1H), 7.82 (d, 2H). ¹⁹F-NMR (CDCl₃, 400 MHz): −78.8.

EXAMPLE 21-[2-bromo-4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]phenyl]sulfanyl-N-ethyl-methanesulfonamideand1-[2-bromo-4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]phenyl]sulfanyl-N,N-diethyl-methanesulfonamide

Potassium carbonate (30 mg) and[2-bromo-4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]phenyl]sulfanylmethanesulfonamide(100 mg, example 1) were placed in a 10 ml flask under argon thenN,N-dimethylformamide (3 ml) was added and the solution cooled to 0° C.Iodoethane (28 mg) was added dropwise over 10 min and the resultingmixture was stirred at room temperature overnight. The mixture waspoured into water extracted with diethyl ether. The organic layer waswashed with 1N HCl, water then brine, dried over sodium sulphate andconcentrated in vacuo to afford a brown solid (150 mg). The cruderesidue was purified with combiflash Rf 200 machine (column of 5 g,eluted with Heptane/EtOAc) to afford1-[2-bromo-4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]phenyl]sulfanyl-N-ethyl-methanesulfonamide(53 mg) as a white solid together with1-[2-bromo-4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]phenyl]sulfanyl-N,N-diethyl-methanesulfonamide(30 mg) as a white solid.

1-[2-bromo-4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]phenyl]sulfanyl-N-ethyl-methanesulfonamide:LCMS (Method A) RT 2.60 min. [M−H]⁻589/591/593; [M-SO2NHEt]⁻481. ¹H NMR(400 MHz, CDCl₃) 1.25 (t, 3H), 3.25 (m, 2H), 3.70 (d, 1H), 4.06 (d, 1H),4.38 (s, 2H), 4.55 (br t, 1H), 7.45 (t, 1H), 7.51 (d, 2H), 7.61 (dd,1H), 7.70 (d, 1H), 7.90 (s, 1H). ¹⁹F-NMR (CDCl₃, 400 MHz): −5 79.4

1-[2-bromo-4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]phenyl]sulfanyl-N,N-diethyl-methanesulfonamide:LCMS (Method A) RT 2.81 min. [M−H]⁻618/619/621. ¹H NMR (400 MHz, CDCl₃)1.15 (t, 6H), 3.30 (m, 4H), 3.60 (d, 1H), 3.97 (d, 1H), 4.22 (s, 2H),7.35 (t, 1H), 7.41 (d, 2H), 7.51 (dd, 1H), 7.60 (d, 1H), 7.80 (s, 1H).¹⁹F-NMR (CDCl₃, 400 MHz): −79.4.

EXAMPLE 3[2-bromo-4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]phenyl]sulfonylmethanesulfonamide

To a solution of[2-bromo-4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]phenyl]sulfanylmethanesulfonamide(50 mg) in dichloromethane was added meta-chloroperbenzoic acid (70%w/w,70 mg) at 0° C. The resulting mixture was allowed to stir at roomtemperature overnight. The organic phase was washed with an aqueoussaturated sodium hydrogen carbonate solution then twice with water,dried over anhydrous sodium sulfate, filtered and evaporated to give awhite solid. The crude residue was purified with Combiflash Rf 200machine (column of 5 g, eluted with DCM/MeOH 5%) to afford the titlecompound as a white solid. LCMS (Method A) RT 2.01 min.[M−H]⁻593/595/597. ¹H NMR (400 MHz, CDCl₃) 3.72 (d, 1H), 4.10 (d, 1H),5.08 (s, 2H), 5.32 (s, 2H), 7.40-8.30 (m, 6H). ¹⁹F-NMR (CDCl₃, 400 MHz):−79.5.

The following compounds were prepared following a similar method to thatdescribed in Example 3:1-[2-bromo-4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]phenyl]sulfonyl-N-cyclopropyl-methanesulfonamide.

EXAMPLE 41-[2-bromo-4-[(5S)-5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]phenyl]sulfanyl-N-ethyl-methanesulfonamide

Step A:(5S)-3-(3-bromo-4-tert-butylsulfanyl-phenyl)-5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazole

5 To a solution of(E)-1-(3-bromo-4-tert-butylsulfanyl-phenyl)-3-(3,5-dichlorophenyl)-4,4,4-trifluoro-but-2-en-1-one(Example 1, Step B, 1.0 g) in chloroform (50 ml) was added1-anthracen-9-ylmethyl quininium chloride (220 mg). The reaction mixturewas cooled at −20° C. then hydroxylamine (50% in water, 0.24 ml) andcesium hydroxide (10 N in water, 0.46 ml) were added simultaneously. Thereaction was stirred at -20° C. for 2 hour and then brought back to roomtemperature. The mixture was diluted with water and extracted withdichloromethane several times; the combined organic layers were driedover MgSO₄ and the solvent evaporated under reduced pressure to obtain abrown gum (1 g) which was purified by with the Combiflash Rf200, (columnof 48 g), eluted with heptane/EtOAc to afford the title product (834 mg)as a yellow solid. LCMS (Method A) RT 1.42 min, [M+Na]⁺544/546/548;¹H-NMR (CDCl₃, 400 MHz): 1.38 (s, 9H), 3.68 (d, 1H), 4.07 (d, 1H), 7.43(t, 1H), 7.50 (s, 2H), 7.59 (dd, 1H), 7.68 (d, 1H), 7.91 (d, 1H).¹⁹F-NMR (CDCl₃, 400 MHz): -79.4. The product was analysed by chiral HPLC(method F): 2.39 min (85.2%), 3.21 min (14.8%).

Step B:2-bromo-4-[(5S)-5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]benzenethiol

To a solution of(5S)-3-(3-bromo-4-tert-butylsulfanyl-phenyl)-5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazole(5.0 g) in toluene (50 mL) was added toluene-4-sulfonic acid (3.33 g)and the reaction was heated at a 110° C. overnight. The reaction wascooled backt down to room temperature and diluted in dichloromethane andwashed with an aqueous saturared NaHCO₃ solution. The organic phase wasdried over MgSO₄ and the solvents removed in vacuo to yield the crudeproduct (5.3 g). The crude product was passed through a pad of silicaand eluting with heptanes/ethyl acetate (8:1). The product obtained wasthen triturated with heptanes to yield the title compound as anoff-white solide (3.5 g). LCMS (Method A) RT 1.33 min,[M−H]⁻468/470/472; ¹H-NMR (CDCl₃, 400 MHz): 3.64 (d, 1H), 4.03 (d, 1H),4.17 (s, 1H, SH), 7.39 (d, 1H), 7.41 (m, 2H), 7.49 (m, 3H), 7.78 (d,1H). ¹⁹F-NMR (CDCl₃, 400 MHz): -79.5.

Step C: N-ethyl-1-sulfanyl-methanesulfonamide

A 50 ml 3-necked round-bottom flask, equipped with a stirrer,thermometer, condenser, dropping funnel was charged with 15 ml ofdiethyl ether and cooled in an MeOH-ice bath. A solution of 2Methylamine (13 ml) in THF was added, then a solution of chloromethanesulfonyl chloride (1.5 g) in diethyl ether (5 ml) was added dropwise tothe well-stirred solution while the temperature was kept below 0° C.After all of the sulfonyl chloride was added, the temperature wasbrought to 25° C., and stirring was continued at this temperature for 2hours. At the end of this time, the reaction mixture was filtered,diluted with diethyl ether. The solution was washed with water, 2N HCLsolution, water, aqueous sodium hydrogen carbonate solution, water,brine and dried over magnesium sulfate, filtered and concentrated undervacuum. The resulting crude N-ethyl chloromethane sulfonamide wasobtained as a clear brown liquid (ca 1.7 g) and used as such in the nextstep. ¹H-NMR (CDCl₃, 400 MHz): 1.2 (t, 3H), 3.2 (m, 2H), 4.41 (s, 2H).

Step D:1-[2-bromo-4-[(5S)-5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]phenyl]sulfanyl-N-ethyl-methanesulfonamide

A solution of2-bromo-4-[(5S)-5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]benzenethiol(150 mg) in DMF (4 ml) was treated with potassium carbonate (71 mg) thenthe resulting mixture was stirred for 5 min at room temperature. Asolution of N-ethyl-1-sulfanyl-methanesulfonamide (105 mg) in DMF (0.5ml) was added and the reaction was stirred at 90° C. for 30 min. Thereaction mixture was poured into water then extracted with ethylacetate, washed with water then brine, dried over magnesium sulfate andthen evaporated under reduced pressure at 40° C. to give the crudeproduct (140 mg). The residue was purified with Combiflash Rf200,(column of 4 g), eluted with heptane/EtOAc to afford the title product(135 mg) as a yellow solid. LCMS and ¹H NMR data corresponded to thoseobtained in Example 2.

The following compounds were prepared following a similar method to thatdescribed in Example 4:1-[2-bromo-4-[(5S)-5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]phenyl]sulfanyl-N-(2,2,2-trifluoroethyl)-methanesulfonamide,1-[2-bromo-4-[(5S)-5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]phenyl]sulfanyl-N-cyclopropyl-methanesulfonamide,1-[2-bromo-4-[(5S)-5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]phenyl]sulfanyl-N-propargyl-methanesulfonamide,1-[2-bromo-4-[(5S)-5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]phenyl]sulfanyl-N-isopropyl-methanesulfonamide.

EXAMPLE 51-[2-bromo-4-[2-(3,5-dichlorophenyl)-2-(trifluoromethyl)-3H-thiophen-4-yl]phenyl]sulfanyl-N,N-diethyl-methanesulfonamide(D-1)

Step A: Ethyl3-(3-bromo-4-tert-butylsulfanyl-phenyl)-5-(3,5-dichlorophenyl)-3-hydroxy-5-(trifluoromethyl)tetrahydrothiophene-2-carboxylate

To a stirring solution of(Z)-1-(3-bromo-4-tert-butylsulfanyl-phenyl)-3-(3,5-dichlorophenyl)-4,4,4-trifluoro-but-2-en-1-one(10 g) in tetrahydrofuran (100 mL). Ethyl 2-sulfanylacetate (6.96 g) andtriethylamine (960 g) was added. The reaction was stirred at RT undernitrogen atmosphere for overnight.

After completion of reaction, monitored by TLC, the reaction mass wasevaporated off under reduced pressure, diluted with water (150 mL) andextracted with ethyl acetate (2×100 mL). The combined organic phaseswere evaporated under reduced pressure and the crude residue waspurified by column chromatography using cyclohexane/ethyl acetate as aneluent to afford the title product (8 g). LCMS (Method A) RT 2.73 min,[M+Na]⁺654.0; ¹H-NMR (CDCl₃, 400 MHz): 7.82 (d, 1H), 7.66 (dd, 1H),7.50-7.52(m, 2H), 7.36-7.38 (m, 2H), 4.71 (s, 1H), 4.57 (s, 1H),4.10-4.16 (q, 2H), 2.99 (d, 1H), 2.87 (d, 1H) 1.356 (s, 9H), 1.15-1.18(t, 3H).

Step B:3-(3-bromo-4-tert-butylsulfanyl-phenyl)-5-(3,5-dichlorophenyl)-3-hydroxy-5-(trifluoromethyl)tetrahydrothiophene-2-carboxylicacid

To a stirring solution of ethyl3-(3-bromo-4-tert-butylsulfanyl-phenyl)-5-(3,5-dichlorophenyl)-3-hydroxy-5-(trifluoromethyl)tetrahydrothiophene-2-carboxylate(8 g) in tetrahydrofuran (100 ml) was added lithium hydroxide (576 mg)in water (5 mL). The reaction was stirred at room temperature forovernight. After completion of reaction monitored by TLC, reaction masswas evaporated off under reduced pressure, diluted with water (15 mL),acidified with HCl solution (5%) and extracted with ethyl acetate (2×100mL). The combined organic layer was washed with water (50 mL), driedover sodium sulphate, evaporated off under reduced pressure. Thusobtained compound (7.5 g) was taken as such for next step withoutfurther purification.

Step C:4-(3-bromo-4-tert-butylsulfanyl-phenyl)-2-(3,5-dichlorophenyl)-2-(trifluoromethyl)-3H-thiophene

To a stirring solution of3-(3-bromo-4-tert-butylsulfanyl-phenyl)-5-(3,5-dichlorophenyl)-3-hydroxy-5-(trifluoromethyl)tetrahydrothiophene-2-carboxylicacid (7.5 g) in pyridine (30 mL) and followed addition ofmethanesulfonyl chloride (3.02 g) at 0° C. and stirring was continued atroom temperature for overnight. After completion of reaction monitoredby TLC, the reaction mass was diluted with water (15 mL), extracted withethyl acetate (3 x 60 mL). The combined organic layer was dried oversodium sulphate and evaporated off under reduced pressure.

Thus obtained 543-bromo-4-tert-butylsulfanyl-phenyl)-3-(3,5-dichlorophenyl)-3-(trifluoromethyl)-6-oxa-2-thiabicyclo[3.2.0]heptan-7-one(6 g) was diluted with in N,N-dimethylformamide (30 mL) heating 10 wasapplied at 100° C. for 2hr. After completion of reaction monitored byTLC, the reaction mass was diluted with water (100 mL) extracted withethyl acetate (3×40 mL). The combined organic layers were washed withwater (2×50 mL) dried over sodium sulphate and evaporated under reducedpressure. The crude residue was purified by column chromatography usingcyclohexane/ethyl acetate as an eluent to afford the title product (4g). LCMS (Method A) RT 2.64 min, [M+H]⁺540.8; ¹H-NMR (CDCl₃, 400 MHz):7.59-7.63 (m, 2H), 7.38-7.41 (m, 2H), 7.25-7.26 (m, 2H), 6.61 (s, 1H),3.83 (d, 1H), 3.60 (d, 1H), 1.34 (s, 9H)

Step D:2-bromo-4-[2-(3,5-dichlorophenyl)-2-(trifluoromethyl)-3H-thiophen-4-yl]benzenethiol

To a stirring solution of4-(3-bromo-4-tert-butylsulfanyl-phenyl)-2-(3,5-dichlorophenyl)-2-(trifluoromethyl)-3H-thiophene(1 g) in methylene chloride (15 mL), boron tribromide (1.37 g) was addedat 0° C. and stirring was continued for 2hr. After completion ofreaction monitored by TLC. The reaction mass was quenched with methanol(0.3 ml) and diluted with ice cold water (10 mL) and extracted with DCM(2×20 mL). The combined organic layers were washed with water (30 mL),dried over sodium sulphate and evaporated under reduced pressure. Thecrude residue was purified by column chromatography usingcyclohexane/ethyl acetate as an eluent to afford the title product (800mg). LCMS (Method A) RT 2.73 min, [M−H]⁺484.8; ¹H-NMR (CDCl₃, 400 MHz):7.37-7.49(m, 5H), 7.08(dd, 1H), 6.40 (s, 1H), 3.70 (d, 1H), 3.51 (d,1H).

Step E: 1-chloro-N,N-diethyl-methanesulfonamide

To a stirring solution of triethylamine (1.1 mL) and N-ethylethanamine(0.76 mL) in dichloromethane (10 mL) −5° C. was addedchloromethanesulfonyl chloride (1 g). The resulting mixture was stirredat room temperature for 2 hours. Reaction mixture was diluted with DCM(5 mL), washed with 10% HCl solution (5 mL), and followed by sodiumbicarbonate solution (5 mL). The combined organic layer was dried oversodium sulphate, concentrated under reduced pressure to afford titlecompounds as yellow oil (900 mg).

¹H NMR (CDCl₃, 400 MHz,): 4.47 (s, 2H), 3.36 (q, 4H), 1.19 (t, 6H)

Step F:1-[2-bromo-4-[2-(3,5-dichlorophenyl)-2-(trifluoromethyl)-3H-thiophen-4-yl]phenyl]sulfanyl-N,N-diethyl-methanesulfonamide(D-1)

To a stirring solution of2-bromo-4-[2-(3,5-dichlorophenyl)-2-(trifluoromethyl)-3H-thiophen-4-yl]benzenethiol(200 mg) in DMF (3 mL) was degassed by bubbling nitrogen for 10 mins Tothis was then added sodium borohydride (14 mg), potassium carbonate (85mg) stirred for 5 mins at room temperature, followed by addition of1-chloro-N,N-diethyl-methanesulfonamide (190 mg). The resulting mixturewas stirred at 90° C. under a nitrogen atmosphere for 4 hours. Thereaction mixture was diluted with water (15 mL) and extracted with ethylacetate (3×30 mL).The combined organic layers were dried over sodiumsulphate, filtered and concentrated under reduced pressure. The crudeproduct was purified by column chromatography eluted withcyclohexane/ethyl acetate (6:4) to obtain the titled compound as a solid(90 mg). LCMS (Method A) RT 5.49 min [M+H]⁺634.0. ¹H NMR (CDCl₃, 400MHz,): 7.65 (d, 1H), 7.54(d, 1H), 7.40 (dd, 2H), 7.38 (d, 1H), 7.28 (dd,1H), 6.58 (m, 1H), 4.25 (s, 2H), 3.83 (d, 1H), 3.62 (d, 1H), 3.4 (q,4H), 1.25 (t, 6H).

EXAMPLE 61-[2-bromo-4-[2-(3,5-dichlorophenyl)-2-(trifluoromethyl)-3H-thiophen-4-yl]phenyl]sulfanyl-N-ethyl-methanesulfonamide(D-2)

To a stirring solution of2-bromo-4-[2-(3,5-dichlorophenyl)-2-(trifluoromethyl)-3H-thiophen-4-yl]benzenethiol(200 mg) in DMF (3 mL) was degassed by bubbling nitrogen for 10 mins Tothis was then added sodium borohydride (14 mg), potassium carbonate (85mg) stirred for 5 mins at room temperature, followed by addition of1-chloro-N-ethyl-methanesulfonamide (161 mg). The resulting mixture wasstirred at 90° C. under a nitrogen atmosphere for 4 hours. The reactionmixture was diluted with water (15 mL) and extracted with ethyl acetate(3 x 30 mL).The combined organic layers were dried over sodium sulphate,filtered and concentrated under reduced pressure. The crude product waspurified by column chromatography eluted with cyclohexane/ethyl acetate(6:4) to obtain the titled compound as a solid (180 mg). LCMS (Method A)RT 5.38 min [M−H]¹ 605.4. ¹H NMR (CDCl₃, 400 MHz,): 7.67 (dd, 1H), 7.56(m, 1H), 7.40 (d, 2H), 7.38 (d, 1H), 7.28 (m, 1H), 6.6 (s, 1H), 5.83(brs, 1H), 4.29 (s, 2H), 3.83 (d, 1H), 3.63 (d, 1H), 3.11(q, 2H), 1.16(t, 3H).

TABLE A Compounds of formula (I-a): (I-a)

Comp No. n R^(5b) R² R¹ ¹H NMR A1 0 Br H H (CDCl₃, 400 MHz): 3.60 (d,1H), 3.98 (d, 1H), 4.35 (s, 2H), 4.70 (br s, 2H), 7.36 (t, 1H), 7.41 (d,2H), 7.52 (dd, 1H), 7.60 (d, 1H), 7.82 (d, 2H) A2 0 Br Et Et (400 MHz,CDCl₃) 1.15 (t, 6H), 3.30 (m, 4H), 3.60 (d, 1H), 3.97 (d, 1H), 4.22 (s,2H), 7.35 (t, 1H), 7.41 (d, 2H), 7.51 (dd, 1H), 7.60 (d, 1H), 7.80 (s,1H) A3 0 Br Et H (400 MHz, CDCl₃) 1.15 (t, 3H), 3.11 (m, 2H), 3.60 (d,1H), 3.97 (d, 1H), 4.28 (s, 2H), 4.55 (br t, 1H), 7.35 (t, 1H), 7.41 (d,2H), 7.51 (dd, 1H), 7.60 (d, 1H), 7.80 (s, 1H) A4 2 Br H H (400 MHz,CDCl₃) 3.72 (d, 1H), 4.10 (d, 1H), 5.08 (s, 2H), 5.32 (s, 2H), 7.40-8.30(m, 6H)

TABLE B Compounds of formula (I-b): (I-b)

Comp No. n R^(5b) R² R¹ ¹H NMR B1 0 Br Et H 1.25 (t, 3H), 3.25 (m, 2H),3.70 (d, 1H), 4.06 (d, 1H), 4.38 (s, 2H), 4.55 (br t, 1H), 7.45 (t, 1H),7.51 (d, 2H), 7.61 (dd, 1H), 7.70 (d, 1H), 7.90 (s, 1H) B2 0 Br CF₃CH₂Et (400 MHz, CDCl₃) 3.69 (d, 1H), 3.85 (m, 2H), 4.05 (d, 1H), 4.41 (s,2H), 5.00 (m, 1H), 7.40-7.90 (m, 1H) B3 0 Br cyclopropyl H (400 MHz,CDCl₃) 0.70-0.80 (m, 4H), 2.55 (m, 1H), 3.69 (d, 1H), 4.05 (d, 1H), 4.41(s, 2H), 5.00 (s, 1H), 7.35 (m, 1H), 7.50 (m, 2H), 7.52 (dd, 1H), 7.70(d, 1H), 7.90 (s, 1H) B4 0 Br isopropyl H (400 MHz, CDCl₃) 1.30 (d, 6H),3.70 (d, 1H), 3.72 (m, 1H), 4.05 (d, 1H), 4.45 (s, 2H), 7.46 (t, 1H),7.51 (s, 2H), 7.61 (dd, 1H), 7.70 (d, 1H), 7.90 (d, 1H) B5 0 Brpropargyl H (400 MHz, CDCl₃) 2.45 (t, 1H), 3.70 (d, 2H), 4.0-4.1 (m,3H), 4.51 (s, 2H), 5.0 (bt, 1H), 7.46 (t, 1H), 7.51 (s, 2H), 7.61 (dd,1H), 7.70 (d, 1H), 7.90 (d, 1H) B6 2 Br cyclopropyl H (400 MHz, CDCl₃)0.80-0.90 (m, 4H), 2.70 (m, 1H), 3.72 (d, 1H), 4.10 (d, 1H), 5.05 (s,2H), 5.32 (s, 1H), 7.40-7.50 (m, 3H), 7.80 (d, 1H), 8.12 (s, 1H), 8.22(d, 1H)

TABLE C Compounds of formula (I-c): (I-b)

Comp No. n R^(5b) R² R¹ RT MS C1 0 Br n-butyl H 2.29 617.12 C2 0 Br1-methoxy-prop-2yl H 2.22 633.09 C3 0 Br 1,1,1-trifluoropropyl H 2.22657.04 C4 0 Br prop-2yl H 2.28 617.09 C5 0 Br tetrahydrofuran-2-ylmethylH 2.2 645.06 C6 0 Br benzyl H 2.28 651.11 C7 0 Br 1-phenylethyl H 2.33665.08 C8 0 Br 1,1-dioxothietan-3-yl H 2.05 664.99 C9 0 Br(6-chloro-3-pyridyl)methyl H 2.2 686.00 C10 0 Br 3-fluorophenyl H 2.27655.05 C11 0 Br 2-pyridylmethyl H 2.13 652.05 C12 0 Br3-methylthietan-3-yl H 2.27 647.03 C13 0 Br 1,1-dimethyl-2- H 2.33663.08 methylsulfanyl-ethyl C14 0 Br 1-oxothietan-3-yl H 2 649.03 C15 0Br norbornan-2-yl H 2.37 655.12 C16 0 Br cyclobutyl H 2.25 615.05 C17 0Br 4-fluorophenyl H 2.26 655.04 C18 0 Br 2-ethoxyethyl H 2.22 633.10 C190 Br propyl H 2.23 603.06 C20 0 Br cyclopropylmethyl H 2.24 615.06 C21 0Br cyclopentyl H 2.3 629.07 C22 0 Br allyl H 2.19 601.10 C23 0 Brcyclobutylmethyl H 2.31 629.11 C24 0 Br 4-trifluoromethylbenzyl H 2.34719.12 C25 0 Br 2-butyl H 2.28 617.10 C26 0 Br2-(1,3-dioxolan-2-yl)ethyl H 2.15 661.07 C27 0 Br cyclopent-3-en-1-yl H2.26 627.10 C28 0 Br [(2R)-tetrahydrofuran-2- H 2.2 645.09 yl]methyl C290 Br 1-ethylpropyl H 2.34 631.07 C30 0 Br oxetan-3yl H 2.07 617.07 C31 0Br 2-methylsulfanylethyl H 2.21 635.07 C32 0 Br tetrahydrothiophen-3-ylH 2.23 647.10 C33 0 Br (2-fluorophenyl)methyl H 2.24 669.06 C34 0 Br(4-methoxyphenyl)methyl H 2.22 681.07 C35 0 Br 2,5-dimethylpyrazol-3-ylH 2.02 655.06 C36 0 Br thietan-3yl H 2.16 633.01 C37 0 Br 2-methoxyethylH 2.1 619.10 C38 0 Br isopropyl ethyl 2.35 631.09 C39 0 Br t-butylmethyl 2.34 631.07 C40 0 Br propyl methyl 2.29 617.09 C41 0 Br ethylethyl 2.29 617.07 C42 0 Br —CH₂—CH═CH—CH₂—CH₂— 2.27 627.04 C43 0 Br—CH₂—CH═CH—CH₂— 2.2 613.03 C44 0 Br —CH₂—CH₂—CH₂—CH(CH₃)— 2.29 629.04C45 0 Br —CH₂—CH₂—CH(CH₃)—CH₂—CH₂— 2.37 643.10 C46 0 Br isobutyl methyl2.35 631.07 C47 0 Br —(CH₂)₄— 2.22 615.07 C48 0 Br —(CH₂)₆— 2.37 643.08C49 0 Br 1-cyanocyclopropyl H 2.08 626.06 C50 0 Br 2-methoxyethyl methyl2.21 633.07 C51 0 Br —(CH₂)₅— 2.31 629.08 C52 0 Br allyl methyl 2.26615.05 C53 0 Br ethyl methyl 2.23 603.05 C54 0 Br —CH₂—CH₂—O—CH₂—CH₂—2.14 631.04 C55 0 Br isopropyl methyl 2.29 617.06 C56 0 Br propargylmethyl 2.2 613.04

TABLE D Compounds of formula (I-d):

Comp No. n R^(5b) R² R¹ ¹H NMR D1 0 Br Et Et (CDCl₃, 400 MHz): 7.65 (d,1H), 7.54(d, 1H), 7.40 (dd, 2H), 7.38 (d, 1H), 7.28 (dd, 1H), 6.58 (m,1H), 4.25 (s, 2H), 3.83 (d, 1H), 3.62 (d, 1H), 3.4 (q, 4H), 1.25 (t, 6H)D2 0 Br H Et (400 MHz, CDCl₃) 7.67 (dd, 1H), 7.56 (m, 1H), 7.40 (d, 2H),7.38 (d, 1H), 7.28 (m, 1H), 6.6 (s, 1H), 5.83 (brs, 1H), 4.29 (s, 2H),3.83 (d, 1H), 3.63 (d, 1H), 3.11 (q, 2H), 1.16 (t, 3H).Biological Examples

This Example illustrates the pesticidal/insecticidal properties ofcompounds of formula (I). Tests were performed as follows:

Spodoptera littoralis (Egyptian Cotton Leaf Worm)

Cotton leaf discs were placed on agar in 24-well microtiter plates andsprayed with aqueous test solutions prepared from 10′000 ppm DMSO stocksolutions. After drying the leaf discs were infested with five L1larvae. The samples were assessed for mortality, anti-feedant effect,and growth inhibition 3 days after infestation. Control of Spodopteralittoralis by a test sample is noted when at least one of mortality,anti-feedant effect, and growth inhibition is better than the untreatedsample.

The following compounds resulted in at least 80% control at anapplication rate of 200 ppm: A1, A2, A3, A4, B1, B2, B3, B4, B5, B6, C1to C47, C49 to C56, D2

Heliothis virescens (Tobacco Budworm):

Eggs (0-24 h old) were placed in 24-well microtiter plates on artificialdiet and treated with aqueous test solutions prepared from 10′000 ppmDMSO stock solutions by pipetting. The samples were assessed for eggmortality, larval mortality and growth inhibition 5 days afterinfestation. Control of Heliothis virescens by a test sample is notedwhen at least one of egg mortality, larval mortality and growthinhibition is better than the untreated sample.

The following compounds resulted in at least 80% control at anapplication rate of 200 ppm: A1, A2, A3, A4, B1, B2, B3, B4, B5, B6, D2

Plutella xylostella (Diamond Back Moth):

24-well microtiter plates with artificial diet were treated with aqueoustest solutions prepared from 10′000 ppm DMSO stock solutions bypipetting. After drying, the plates were infested with L2 larvae (10 to15 per well). The samples were assessed for mortality and growthinhibition 5 days after infestation. Control of Plutella xyllostella bya test sample is noted when at least one of mortality and growthinhibition is better than the untreated sample.

The following compounds resulted in at least 80% control at anapplication rate of 200 ppm: A1, A2, A3, A4, B1, B2, B3, B4, B5, B6, C1to C23, C25 to C34, C36 to C56, D2

Diabrotica balteata (Corn Rootworm):

24-well microtiter plates with artificial diet were treated with aqueoustest solutions prepared from 10′000 ppm DMSO stock solutions bypipetting. After drying, the plates were infested with L2 larvae (6 to10 per well). The samples were assessed for mortality and growthinhibition 5 days after infestation. Control of Diabrotica balteata by atest sample is noted when at least one of mortality and growthinhibition is better than the untreated sample.

The following compounds resulted in at least 80% control at anapplication rate of 200 ppm: A1, A2, A3, A4, B1, B2, B3, B4, B5, B6

Diabrotica balteata, (Corn Rootworm)

Maize sprouts, placed on an agar layer in 24-well microtiter plates weretreated with aqueous test solutions prepared from 10′000 ppm DMSO stocksolutions by spraying. After drying, the plates were infested with L2larvae (6 to 10 per well). The samples were assessed for mortality 4days after infestation.

The following compounds resulted in at least 80% mortality at anapplication rate of 200 ppm: C1 to C56, D2

Myzus persicae (Green Peach Aphid):

Sunflower leaf discs were placed on agar in a 24-well microtiter plateand sprayed with aqueous test solutions prepared from 10′000 ppm DMSOstock solutions. After drying, the leaf discs were infested with anaphid population of mixed ages. The samples were assessed for mortality6 days after infestation.

The following compounds resulted in at least 80% mortality at anapplication rate of 200 ppm: A3, B1, B4, C1, C12, C15, C16, C18, C19,C22, C23, C25, C26, C27, C28, C30, C32, C36, C37, C39, C40, C41, C50,C52, C53, C55

Thrips tabaci (Onion Thrips):

Sunflower leaf discs were placed on agar in 24-well microtiter platesand sprayed with aqueous test solutions prepared from 10′000 ppm DMSOstock solutions. After drying the leaf discs were infested with a thripspopulation of mixed ages. The samples were assessed for mortality 6 daysafter infestation.

The following compounds resulted in at least 80% control at anapplication rate of 200 ppm: A1, A2, A3, B1, B2, B3, B4, B5, B6, C1 toC9, C11, C12, C14, C15, C16, C18 to C23, C25 to C34, C36 to C56

Tetranychus urticae (Two-Spotted Spider Mite):

Bean leaf discs on agar in 24-well microtiter plates were sprayed withaqueous test solutions prepared from 10′000 ppm DMSO stock solutions.After drying the leaf discs were infested with a mite population ofmixed ages. The samples were assessed for mortality (mobile stages) 8days after infestation.

The following compounds resulted in at least 80% control at anapplication rate of 200 ppm: 15 A1, A2, A3, A4, B1, B2, B3, B4, B5, B6,C1, C3, C4, C5, C8, C11, C12, C14, C16, C18 to C23, C25 to C28, C30 toC32, C36 to C38, C40, C41, C43, C47, C48, C50, C52 to C55, D1

Test to Determine Biological Safety Profile

Spodoptera littoralis (Egyptian Cotton Leafworm)

Cotton plants in the 5 leaf stage (around 5 weeks old) are treated in anautomated turn table spray chamber. Plants were stored in the greenhouseat 26° C. and 14h day length during the whole test period. 2, and 16days after treatment, 4 leaves from each sample were excised, placedinto 14cm plastic petri dishes on wet filter paper. The infestation of10 L-3 Spodoptera littoralis is made immediately afterwards. The sampleswere assessed for mortality, growth inhibition and anti-feedant effectafter an incubation period of 6 days at 27° C. (without light). Controlof Spodoptera littoralis by a test sample is noted when at least one ofmortality, growth inhibition and anti-feedant effect is higher than theuntreated sample.

Tetranychus urticae (Two Spotted Spider Mite)

Bean plants are infested with mite populations of mixed ages. 1 dayafter infestation, plants are treated in a spray chamber with dilutedtest solutions. 1 and 10 days later, samples are checked for mortality.

The invention claimed is:
 1. A compound of formula I

wherein A ¹ is C—R^(5b); A², A³ and A⁴ are independently of one anotherC—H, C—R^(5a) or nitrogen; Y₁—Y₂—Y₃ is —C═N—O—, —C═N—S—, —C═N—CH₂—,—C═CH—O— or —N—CH₂—CH₂—, —C═CH—S—; n is 0, 1 or 2; R¹ is hydrogen,C₁-C₈alkyl, C₁-C₈alkoxy or C₁-C₈alkylcarbonyl or C₁-C₈alkoxycarbonyl; R²is hydrogen, C₁-C₈alkyl or C₁-C₈alkyl substituted by one to five R⁶,C₂-C₈alkenyl or C₂-C₈alkenyl substituted by one to five R⁶, C₂-C₈alkynylor C₂-C₈alkynyl substituted by one to five R⁶, C₃-C₁₀cycloalkyl orC₃-C₁₀cycloalkyl substituted by one to five R⁷, aryl-C₁-C₄alkylene oraryl-C₁-C₄alkylene wherein the aryl moiety is substituted by one to fiveR⁸, heterocyclyl-C₁-C₄alkylene or heterocyclyl-C₁-C₄alkylene wherein theheterocyclyl moiety is substituted by one to five R⁸, aryl or arylsubstituted by one to five R⁸, heterocyclyl or heterocyclyl substitutedby one to five R⁸; or R¹ and R² together with the nitrogen atom to whichthey are bound form a 4- to 7-membered cycle containing carbon atoms asring members and optionally containing one oxygen atom or one sulfuratom optionally oxidized as a ring member and wherein the cycle isoptionally substituted by 1 to 5 groups independently selected fromhalogen, C₁-C₄alkyl and C₁-C₄alkoxy; R³ is C₁-C₈haloalkyl; R⁴ is aryl oraryl substituted by one to five R⁹, or heteroaryl or heteroarylsubstituted by one to five R⁹; each R^(5a) is independently halogen,cyano, nitro, C₁-C₈alkyl, C₁C₈haloalkyl, C₂-C₈alkenyl, C₂-C₈haloalkenyl,C₂-C₈alkynyl, C₂-C₈haloalkynyl, C₃-C₁₀cycloalkyl, C₁-C₈alkoxy,C₁-C₈haloalkoxy, C₁-C₈alkylthio, C₁-C₈haloalkylthio,C₁-C₈alkylsulfinyl-, C₁-C₈haloalkylsulfinyl-, C₁-C₈alkylsulfonyl- orC₁-C₈haloalkylsulfonyl-; R^(5b) is halogen, C₁-C₈alkyl, C₁-C₈haloalkyl,C₂-C₈haloalkenyl, C₂-C₈alkynyl, C₂-C₈haloalkynyl,C₃-C₁₀cycloalkyl orC₃-C₁₀cycloalkyl substituted by one to five R⁷, or R^(5a) and R^(5b) onadjacent carbon atoms together form a —CH═CH—CH═CH— bridge or a—N═CH—CH═CH— bridge; each R⁶ is independently halogen, cyano, nitro,hydroxy, C₁-C₈alkoxy, C₁-C₈haloalkoxy, C₁-C₈alkylcarbonyl,C₁-C₈alkoxycarbonyl, mercapto, C₁-C₈alkylthio, C₁-C₈haloalkylthio,C₁-C₈alkylsulfinyl, C₁-C₈haloalkylsulfinyl, C₁-C₈alkylsulfonyl, orC₁-C₈haloalkylsulfonyl; each R⁷ is independently halogen, cyano,C₁-C₈alkyl or C₁-C₈haloalkyl; each R⁸ and R⁹ is independently halogen,cyano, nitro, C₁-C₈alkyl, C₁-C₈haloalkyl, C₂-C₈alkenyl,C₂-C₈haloalkenyl, C₂-C₈alkynyl, C₂-C₈haloalkynyl, hydroxy, C₁-C₈alkoxy,C₁-C₈haloalkoxy, mercapto, C₁-C₈alkylthio, C₁-C₈haloalkylthio,C₁-C₈alkylsulfinyl, C₁-C₈haloalkylsulfinyl, C₁-C₈alkylsulfonyl,C₁-C₈haloalkylsulfonyl, C₁-C₈alkylcarbonyl, C₁-C₈alkoxycarbonyl, aryl oraryl substituted by one to five R¹⁰ or heterocyclyl or heterocyclylsubstituted by one to five R¹⁰; each R¹⁰ is independently halogen,cyano, nitro, C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy orC₁-C₄haloalkoxy; or a salt or N-oxide thereof.
 2. A compound accordingto claim 1, wherein Y₁—Y₂—Y₃ is —C═N—O—.
 3. A compound according toclaim 1, wherein Y₁—Y₂—Y₃ is —C═N—CH₂—.
 4. A compound according to claim1, wherein Y₁—Y₂—Y₃ is —C═CH—O—.
 5. A compound according to claim 1,wherein Y₁—Y₂—Y₃ is —N—CH₂—CH₂—.
 6. A compound according to claim 1,wherein Y₁—Y₂—Y₃ is —C═N—S—.
 7. A compound according to claim 1, whereinY₁—Y₂—Y₃ is —C═CH—S—.
 8. A compound according to claim 1, wherein R^(5b)is halogen or methyl.
 9. A compound according to claim 1, wherein R² isC₁-C₄alkyl or C₁-C₄alkyl substituted by one to five groups independentlyselected from halogen, cyano, C₁-C₄alkoxy and C₁-C₄alkylthio,C₂-C₄alkenyl or C₂-C₄alkenyl substituted by one to five halogen,C₂-C₄alkynyl or C₂-C₄alkynyl substituted by one to five halogen,C₃-C₆cycloalkyl or C₃-C₆ cycloalkyl substituted by one to five groupsindependently selected from halogen, methyl and halomethyl,phenyl-C₁-C₂alkylene or phenyl-C₁-C₂alkylene wherein the phenyl moietyis optionally substituted by one to three substituents independentlyselected from halogen, cyano, C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxyand C₁-C₄haloalkoxy, pyridyl-C₁-C₂alkylene or pyridyl-C₁-C₂alkylenewherein the pyridyl moiety is optionally substituted by one to threesubstituents independently selected from halogen, cyano, C₁-C₄alkyl,C₁-C₄haloalkyl, C₁-C₄alkoxy and C₁-C₄haloalkoxy, thietanyl,oxo-thietanyl, dioxo-thietanyl, oxetanyl, tetrahydrofuranyl,thietanyl-methyl, oxo-thietanyl-methyl, dioxo-thietanyl-methyl, andoxetanyl-methyl.
 10. A compound according to claim 1, wherein R² isC₁-C₄alkyl or C₁-C₄alkyl substituted by one to five groups independentlyselected from halogen, cyano, methoxy and methylthio, C₂-C₄alkenyl orC₂-C₄alkenyl substituted by one to five halogen, C₂-C₄alkynyl orC₂-C₄alkynyl substituted by one to five halogen, C₃-C₄cycloalkyl orC₃-C₄cycloalkyl substituted by one to five groups independently selectedfrom halogen, methyl and halomethyl, pyridylmethyl or pyridylmethylwherein the pyridyl moiety is substituted with one to four groupsselected from halogen, cyano, methyl, halomethyl, methoxy andhalomethoxy.
 11. A compound according to claim 1, wherein R¹ and R²together with the nitrogen atom to which they are bound form a 4- to7-membered cycle containing carbon atoms as ring members and optionallycontaining one oxygen atom or one sulfur atom optionally oxidized as aring member and wherein the cycle is optionally substituted by 1 to 5groups independently selected from halogen, C₁-C₄alkyl and C₁-C₄alkoxy.12. A compound according to claim 1, wherein R³ is chlorodifluoromethylor trifluoromethyl.
 13. A compound according to claim 1, wherein R⁴ isgroup A1

wherein X is C—R¹² or nitrogen and each R¹² is independently hydrogen,halogen or trihalomethyl, wherein at least two R¹² are not hydrogen. 14.A compound according to claim 1, wherein A¹ is C—R^(5b); A², A³ and A⁴are C—H; Y₁—Y₂—Y₃ is —C═N—O—, —C═N—S—, —C═N—CH₂—, —C═CH—O—, —N—CH₂—CH₂—or C═CH—S—; R¹ is hydrogen; R² is C₁-C₄alkyl or C₁-C₄alkyl substitutedby one to five groups independently selected from halogen, cyano,methoxy and methylthio, C₂-C₄alkenyl or C₂-C₄alkenyl substituted by oneto five halogen, C₂-C₄alkynyl or C₂-C₄alkynyl substituted by one to fivehalogen, C₃-C₄cycloalkyl or C₃-C₄cycloalkyl substituted by one to fivegroups independently selected from halogen, methyl and halomethyl,pyridylmethyl or pyridylmethyl wherein the pyridyl moiety is substitutedwith one to four groups selected from halogen, cyano, methyl,halomethyl, methoxy and halomethoxy; or R¹ and R² together with thenitrogen atom to which they are bound form a 4- to 7-membered cyclecontaining carbon atoms as ring members and optionally containing oneoxygen atom as a ring member; R³ is trifluoromethyl; R⁴ is group A1

wherein X is C—R¹² and each R¹² is independently hydrogen, halogen ortrihalomethyl, wherein at least two R¹² are not hydrogen; R^(5b) ishalogen or methyl.
 15. A compound according to claim 14, wherein A¹ isC—R^(5b); A², A³ and A⁴ are C—H; Y₁—Y₂—Y₃ is —C═N—O—, —C═N—S—,—C═N—CH₂—, —C═CH—O— or —N—CH₂—CH₂— or C═CH—S—; R¹ is hydrogen; R² ismethyl, ethyl, propyl, butyl, fluoroethyl, fluoropropyl, fluorobutyl,difluoroethyl, difluoropropyl, difluorobutyl, trifluoroethyl,trifluoropropyl, trifluorobutyl, cyclopropyl, cyclobutyl, allyl,propargyl, pyridylmethyl; R³ is trifluoromethyl; R⁴ is group A1, whereinX is C—R¹² and each R¹² is independently hydrogen, halogen ortrihalomethyl, wherein at least two R¹² are not hydrogen; R^(5b) ischloro, bromo or methyl.
 16. A mixture comprising a compound of formulaI* and a compound of formula I**

wherein Y₁—Y₂—Y₃ is —C═N—O—, —C═N—S—, —C═N—CH₂—, —C═CH—O—, —N—CH₂—CH₂—or —N—CH₂—CH₂—; and A¹, A², A³, A⁴, R¹, R², R³, R⁴ and n are as definedin claim 1, and wherein the molar proportion of the compound of formulaI** compared to the total amount of both the compound of formula I* andI** is greater than 50%.
 17. A mixture according to claim 16, whereinA¹, A², A³, A⁴, Y¹, Y², Y³, R¹, R²R³, R⁴ and n are as defined in claim13, and wherein the molar proportion of the compound of formula I**compared to the total amount of both the compound of formula I* and I**is greater than 70%.
 18. A mixture according to claim 16, wherein A¹,A², A³, A⁴, Y¹, Y², Y³, R¹, R², R³, R⁴ and n are as defined in claim 14,and wherein the molar proportion of the compound of formula I** comparedto the total amount of both the compound of formula I* and I** isgreater than 70%.
 19. A compound of formula Int-I

wherein Y₁—Y₂—Y₃ is —C═N—O—, —C═N—S—, —C═N—CH₂—, —C═CH—O—, or—N—CH₂—CH₂— or —N—CH₂—CH₂—; and A¹, A², A³, A⁴, R³, R⁴ and n are asdefined for the compound of formula I in claim 1, and R is OH orhalogen, or a salt of N-oxide thereof; or a compound of formula Int-II

wherein A¹, A², A³, A⁴, R¹, R² and n are as defined for the compound offormula I in claim 1 provided that not both of R¹ and R² are H, andX^(B) is a leaving group or X^(B) is cyano, formyl or acetyl, or a saltof N-oxide thereof; or a compound of formula Int-III

wherein A¹, A², A³, A⁴, R¹, R² and n are as defined for the compound offormula I in claim 1, or a salt of N-oxide thereof; or a compound offormula Int-IV

wherein A¹, A², A³, A⁴, R¹, R², R³, R⁴ and n are as defined for thecompound of formula I in claim 1, or a salt of N-oxide thereof.
 20. Aninsecticidal, acaricidal, nematicidal or molluscicidal compositioncomprising an insecticidally, acaricidally, nematicidally ormolluscicidally effective amount of a compound of formula (I) as definedin claim 1 and optionally at least one additional compound havingbiological activity.
 21. A combination product comprising a pesticidallyeffective amount of a component A and a pesticidally effective amount ofcomponent B, wherein component A is a compound of formula (I) as definedin claim 1, and component B is at least one compound selected from thegroup consisting of imidacloprid, enrofloxacin, praziquantel, pyrantelembonate, febantel, penethamate, moloxicam, cefalexin, kanamycin,pimobendan, clenbuterol, fipronil, ivermectin, omeprazole, tiamulin,benazepril, milbemycin, cyromazine, thiamethoxam, pyriprole,deltamethrin, cefquinome, florfenicol, buserelin, cefovecin,tulathromycin, ceftiour, selamectin, carprofen, metaflumizone,moxidectin, methoprene, S-methoprene, clorsulon, pyrantel, amitraz,triclabendazole, avermectin, abamectin, emamectin, eprinomectin,doramectin, selamectin, nemadectin, albendazole, cambendazole,fenbendazole, flubendazole, mebendazole, oxfendazole, oxibendazole,parbendazole, tetramisole, levamisole, pyrantel pamoate, oxantel,morantel, triclabendazole, epsiprantel, fipronil, lufenuron, ecdysoneand tebufenozide.